@Austin Montgomery  Transferring the property into a trust, particularly an anonymous land trust within a Series LLC, would be a way to avoid the Due on Sale clause while also allowing you to utilize your LLC strictly for paying rents, contractors and doing business. 

I know that there are some strict restrictions for STR in the city of Orlando.

My advice, go to the Agent's broker, if he doesn't have one go to the board of realtor's and ask for assistance, there are strict rules for fulfilling dual roles in a transaction. 2.

At the smaller multi-fam syndication, you aren't competing with them (in some markets, you won't be competing with REITs on SFHs as well - or different types of SFH as REITs have a pretty strict buy box). 

If you don't do that, with strict boxes around different scenarios, you're 100% going to get mixed up and mush Freddie and FHA and Fannie guidelines together into a confused basket of confetti that makes no sense.

When you speak of Realtors as a good source to find buyers, are you speaking strictly investors/landlords connections, or do some agents also help sell this to your “average Joes” who are looking to move in long term?

This will likely continue, Houston has a diverse employment base, it's not longer strictly funded by oil.That being said, Houston is huge and a lot of it is in flood zones. 

The solution to that is strict rent payment requirements, and at the first sign of trouble, inspecting the unit, which should be happening on a regular basis anyway.

Most of those buildings have pretty strict rules about STR so you're unlikely to find someone.Good luck though. 

I would also recommend setting strict screening criteria of what you are looking for in a potential tenant.