I just feel like going deep into rabbit holes like this aren't worth my time and effort tbh.

So instead of trying to force square peg's in round holes, maybe consider better uses of your energy, how to better get round peg's that fit nice and neatly, and at a nice profit I might add. 

., cleanliness, basic landscaping for SFHs, holes in the wall, doorknobs broken, etc.).

I have found a honey hole and want to keep this relationship going well…..so what would you do?

I would then get a inspection of the foundation and house but then I'm 1k in the hole without any promise of purchase beforehand.

Closing up holes is part of preventing them from coming back in and also preventing them from traveling throughout the house.  

Hi Matthew,I second the idea of skimming through the beautiful rabbit hole of Pinterest to get ideas and brainstorm.  

If it was for NONPAYMENT OF RENT, there are loop holes there and they can drag it out.

But if you manage the property poorly or squander the cash flow, you can dig yourself into a hole quickly.Cash out the equity?

It sounds like DST may be risky and best avoided. this is my thought process :if you dont have replacement property --> DST is goodif capital gain is less than 100k --> just pay taxbest USE for 1031 in my opinion-->STR in hawaii/tahoe/ski resort/FL beachif you want to sell in phases (as REIT stock) ---> Sec 721 is good rarely the best option is going to TIC/syndication, this would go to another rabbit hole of headache.