But for someone thinking about scaling and possibly repeating the strategy in multiple markets.. say, Austin or San Antonio-going the investment property route might provide more long-term flexibility.Have you noticed lenders trending toward stricter definitions of “second homes” versus investment properties?

I've been interested in orchard and timber investment for a while, but haven't done much work to go that route.

Given the abatement option could you continue to occupy 15% of the building with commercial tenants while the rest of the building is converted or is that a logistical nightmare/ideally are you seeking different long term commercial tenants if you go that route? 

Perhaps I would have gone that route if I had started younger...

Yep for one especially in the early stages a hard credit pull would not be useful, just have them do soft checks for the time being and opt out of credit solicitation: www.optoutprescreen.com I could be biased... that said typically working with one lender than can help regardless of where you're looking and having a relationship with that will provide the easiest and most cost effective route long term. 

If you do the "do it yourself" route, you'll have to navigate your own paperwork.  

I’m leaning towards the Fannie Mae route but have no idea the process to transfer it to your LLC later.

Glad it worked out for you with the LTR route!

Also, I recommend you have a banking relationship with Wells and Chase prior to shopping if that's the route you're definitely going to take. 

@Matt R. out of 1500 properties we are 98.5% occupied!