@jason-pratt
1 - just addressing one dimension of your first question: my mentor taught me to start with the minimum subscription tech stack necessary and let pain tell you when it's time to invest money in more technology---that's been good advice so far to limiting costs to only those items that bring a ROI through more deals and more efficiency. you can pretty much do everything for free when you start out this land investing journey---soon as you start making deals, the pain ratchets up, telling you where to upgrade next.
2 - i'd put my money on not taking action as the most common pitfall
3 - recommend do the wholesale deals once you have a chunk of properties under your belt. You need confidence on the process, due diligence, and pricing, as well as having your systems established, before you can confidently make deals with other investors. You could easily tie up lots of capital on marginal deals if you skip the training wheels phase. On the other hand, if acquisition is just too slow through your direct mail efforts, there is something to be said for dipping your toe in with wholesale deals just to get the buy/sell experience---caveat emptor is all.
4 - no i wouldn't---concur with Seth's comment---do some small deals yourself, follow and learn the processes, ask for help from other investors (feel free to ask me). you'll undoubtedly make some mistakes---if you are not, then you are making the biggest mistake of all, which is avoiding making yourself uncomfortable. Use realtors later on if you'd like once you have the experience to make an informed decision on ROI and efficiency and can properly screen for a good agent.

Jason Wollbrink I take lots of podcast notes. Apologize for the wall of words to follow, but if anyone's interested, these are my Short Term Rental notes...

Book through Vrbo and/or Airbnb. You can use Google Calendar for appointments, as it syncs with gmail. It allows you to share booking schedules with partners, cleaning crew, etc.

Expenses to Account For:
Airbnb charges a 3-5% service fee every time a booking is completed.
HomeAway charges hosts for listing homes on the site. People planning to use the HomeAway site regularly can pay $349.00 annually to advertise their property and are not charged a commission for each booking.
Vrbo fee if you also list on that site.
Allowance for maintenance (7-10%) and CAPEX (10%). If there’s an HOA, you might add another 10% to a normal CAPEX for assessments.
When running numbers, calculate whether you could break even with a 30% management fee just in case.
Account for wear and tear, replacement of furniture, dishes, lamps, etc.
Cleaning fee (billed to tenants)
Cleaning service can be your eyes and ears.
Occupancy tax (billed to tenants and collected by Vrbo). Make sure there’s not a hotel occupancy tax.
Property insurance
You need to get short-term rental property insurance for Airbnb.
CBIZ Vacation Rental Insurance
Commercial insurance - around $770/year
HOA/Assessments
Utilities (electricity, sewer/water, cable, wifi)
“Beach service” (beach vacation rentals)
Look into door code system (Kaba, August Smart Locks, erentallock.com, ResortLock/RemoteLock)

For the state of Florida, you must pay:
Florida Transient Rental Tax - 6% of listing price
Florida Discretionary Sales Surtax - .5% - 1.5% of listing price
County Tourist Development Tax - location dependent - 2% - 5% of listing price (Okaloosa, not Bay)
On the Gulf Coast, consider hail/wind insurance.

Back-of-Napkin Approximation for Bookings (Northwest FL):
June, July, and August: 25 bookings per month
100 bookings or more for the rest of the year
November through February are slow

Furnishing the Unit:
Check out rent-to-own furniture.

Management/Data Resources:
TurnoverBnb - allows you to remotely manage cleaners from an app - they have pre-approved cleaners, or you can bring on your own
iGMS - vacation rental software - allows you to manage the vacation rental business, automate emails, guest messaging, has an app.
Wheelhouse - helps you figure out/automate pricing for Airbnb rentals and adjusts pricing depending on how far out the rental timeline is.
Smartbnb.io - property management platform - automates a lot of the messaging
Local property management - rented.com, guesty.com
Freetobook - free online booking platform
Ownerreservations.com - vacation rental software that manages your channel listings

Finding Local Cleaning Services:
Thumbtack.com
Taskrabbit.com
Handy.com
Angie’s List
Nextdoor.com

Further reading:
https://www.biggerpockets.com/blog/6-steps-started-airbnb

Kenny B, I can't give any advice on what's legal or not, but I have some limited experience with this, having put three different properties under contract with the intention of double closing, so far. Check out the advice I got on this thread about this topic: https://retipster.com/forum/topic/310/what-is-the-right-document-to-use-for-a-double-closing

One of my three double closing deals did close very quickly (both purchase and resale), as intended, within 60 days of signing my purchase PSA. Another deal, I put under contract in early September, found a buyer very quickly thereafter (within a week or two), but I'm finally going to close on the purchase (and then the resale) this coming week -- probably just at or over the 180 day mark. The third deal, after about 4 to 6 weeks of trying, I was unable to find a buyer due to particular attributes of the property that I was unaware of prior to putting it under contract (particular HOA restrictions that were very unpopular with prospective buyers), so I pulled out of the purchase contract, after incurring costs for title research only. I was very glad that I, in effect, used the option / double closing approach for that one, rather than closing on my purchase before marketing it, only to find out then that the value was not what I'd hoped.

Based on those experiences, at this point I'd recommend:

Having 180 days on both your purchase and resale PSAs -- hoping you won't need that much, but being glad it's there if and when you do.

Including language in your purchase PSA that gives you solid recourse if your Seller tries to back out after signing (i.e. making them liable for your legal fees if you have to go to court to enforce the contract, and you prevail). I posted about this on another thread a few months back that I can find and link to if you're interested.

Having language in your resale PSA that ensures you're not liable if you're unable to acquire the property and are therefore unable to sell it to your Buyer. In my view (as a non-lawyer and non-expert), this one seems like the most important point out of all these. Check out the specific advice Braden C gave me on this point in that thread I linked to above.

Lastly, to your second question, about how you market a property that you don't own, when you don't have a cash buyers list. I'm very interested to hear what others say about this too, but from my experience: on one deal I called custom home builders in the area and explained that I had a parcel under contract and would offer it at a very competitive price for a buyer willing to do a double close; the others I posted on Facebook with a title saying "COMING SOON..." or "PREVIEWING - Lot for Sale...", or the like. With the latter approach, I did find it awkward in communicating with prospective buyers, trying to straddle the line between being honest about the situation, but not over-sharing unnecessary details that would just scare some buyers off ("what do you mean you don't own it?"). Not sure I've found the "perfect" approach for that one yet.

@brian-sylvester

Personally I wasted lots of money buying templates and paying for ready made website. I’m just now on my second year and finally getting a gripe on how I operate and who I am as an investor. I’m finally ready to have a website because I know where I want my business to be in the foreseeable future. If you’re on a tight budget I’d get a few deals under your belt before you invest a lot of money on websites.

Greg Morris there is one lender I know of that works in Michigan and Wisconsin that openly advertises that they do land loans, but knowing how banks work, I'm 100% sure that's not a blanket statement. It doesn't mean they will do ANY loan on ANY piece of land, there are still a lot of qualifiers and boxes that need to be checked. All banks will use the 5 C's of Credit (among other things) to make sure the overall credit is strong enough to mitigate their risk in the deal.

In many cases, a lender won't necessarily turn down a deal if ONE of these metrics is weak (for example, if the collateral value is hard to verify, which is common with vacant land), but if this is the case, they better be able to identify a lot of other financial strength in order to approve a loan (e.g. - the borrower should be very strong financially, or they should have additional collateral to support to credit, so they won't have to rely on the collateral value or the land if everything falls apart).

Don Yost I've heard Austin is one of the most popular destinations for people from the high-tech industry. UHUAL publishes a state-wide migration report annually but not city-wise, I guess we can figure out from that... Here is the link for 2020 Migration Trends: U-Haul Ranks 50 States by Migration Growth

https://www.uhaul.com/Articles...

Angela Stokes To piggyback on Seth's comment, the process you use is probably about as important as the site you hire from.  Over a period of about two weeks, I sent out multiple emails requiring attention to detail in their response, asked them to fill out a google form survey, did a (paid) research tasking to evaluate their results, and finally an interview with my first choice to make sure it would be a good fit.

Seth Williams Thanks for the warm welcome-- Actually one of my other property managers lost his license for some sort of accounting shenanigans. So I am qualified to answer all my-property-manager-has-gone-off-the-reservation questions... Yet another bonus of land investing..   

Hey Jeff! Welcome to the forum!

- I think the standard "best practice" is to start an LLC, but it's not a requirement. If you already have an LLC, you could start with that or form a new one. Honestly though, if you feel bogged down by this one step, don't let it keep you from moving forward and taking action. There's no rule saying you can't get started with your personal name and come back and form an LLC once you've proven the concept to yourself.

- That depends a lot on what format the list comes in (and there are a lot of different formats these can come in). You're right, some of them are VERY dense and hard to get through... but if you can do it, you'll be one of the few who actually went so far as to get access to those motivated sellers.

- I would expect a handful of angry responses (and if you send them to a voicemail greeting of a virtual receptionist, you'll never have to talk to them anyway), a handful of people who call and hang up, and a handful of people who happily accept your offers. In terms of the quantity of each, it depends a lot on how much mail you send out in total, how well you've scrubbed your list, and how good your offers are.

I'm glad to see you've found some value in REtipster, that's really encouraging to hear!

Sean Webster you could use the title company to help you with this... if anyone would be qualified to handle this job and know what they're doing, it's them (or at the very least, they could point you to the right person who can help).

Cameron Bennett I've used GoDaddy before. It was fine. Given the issues you're asking about, though, this sounds like more of a question about getting your domain name set up with the right hosting account, and then getting a good theme that will allow you to set up this kind of thing.

There are easy (and somewhat expensive) ways to do this, and there are more complicated (and cheaper) ways to handle this.

With the issues you're mentioning, it sounds like you might want to go for some of the easier options. You can waste A LOT of time monkeying around with websites, especially if you don't really know what you're doing (this was the mistake I made with my first couple of websites). There's a lot of value in just getting the job done quickly and correctly the first time.

Seth Williams

Hi Seth,

Not sure if it's an option or not but if you stumble upon some of these less desirable deals for your scale I'd love to try a few to get my feet wet. I've only gone through my first couple of mailers and am still waiting for a spot to get my feet wet. If not I completely understand but I figure it can't hurt to ask.

Gary Skale

Cool...so you essentially don’t mail to any sellers that purchased the property within the last 5 years?  I never thought about the currently listed properties.  Thanks for your response!  

Linda Hastings said:

rt time th

 HelloSign is a solid product.  

Nicolas McNaughton

Hi, 

  Please reach out to me with details  

Thanks

Mike

After all these years, my favorite remains The 7 Habits of Highly Effective People.

I used to worry about my phone running out of battery as I go about my business. Getting a portable power bank for my phone lowered my anxiety level significantly. I no longer have to stop someone else on the phone and apologize that the call may drop soon. 😄