The transition is going to be key... the less confused the tenants are, the better of a start you will have in gaining their trust moving forward. 

Networking with other investors and attending local meetups can help you gain advice and opportunities.

There are good tax benefits, but you should really decide on whether you want to own and operate a business that requires as much upkeep as STR before exploring it further.

I recommend making an LLC since there is so much benefits to it.

Plus to realize that appreciation it costs you money to sell, refinance, and potentially pay taxes on the gain. 

I have suspended Passive Activity loss that would reduce the gain, but not eliminate the gain from tax POV.

I have seen instances where a 1031 exchange was not required such as1) The overall gain from the sale of the investment property was very small or even negative2) The taxpayer had enough passive loss carryforwards to offset the gain.A 1031 exchange is a very powerful tool put it has to make sense before going forward.

There are benefits to using the LLC, holding company, or trust, but they all come with costs and add complexity to your life that is often unwarranted.

The more you can help investors mitigate risk, confirm their underwriting, and/or illuminate potential gains or pitfalls; the more successful you'll be.

Let's see how we can connect and hopefully can provide benefit to both of us especially since we are local.