I literally know nothing on this subject so any input is appreciated.

Depending on the built in gain and how long you've lived there, you should be able to sell your current primary tax-free and roll any gains from that into your new primary residence, that is IRC section 121.Is there a set amount of time before you can move into the rental as your primary?

The chimney contractor replaced the cap, but requires the branches be trimmed before he can perform repairs on the chimney because it is still leaking into the fire place after the cap was replaced. 

This other thread was more focused on the initial subdivision and purchasing process.  

☝️Don't be cringy...That's literally what an attorney said on a recent REI Zoom.

It is big impact on short stays and less impact on longer stays. 

Seller who had been on the property and had gone through divorce.

Have you decided on which market you'll be investing in and what strategy you'll use?

He was overwhelmed at first with all the "insider" stuff: the 1031 exchanges, cash-on-cash returns, and figuring out what an ideal cap rate is, especially in a hot market like Dallas.

It really depends on what your goals are.