There is an unfinished basement which will likely be permitted to convert into an ADU but might trigger the installation of a fire sprinkler system ($30k).

As mentioned above it depends on the metro but I would make sure I was comfortable with the LTR rate before pulling the trigger on an STR. 

The risks, such as triggering a "due on sale" clause and complicating your taxes, often outweigh the benefits. 

@John Bertolon we’ve noticed over the years that any decent rent increase triggers “stupid-trip” repair requests, change of owners or not.

We are probably going back into acquisition mode here shortly but want to shore up things before that happens.I also spent the last few months building out a centralized notion to manage all the document, to dos, etc but have pulled the trigger on VAs as the cash flow isn't there yet to support someone full time.

Which CAN trigger the due on sale clause. 

I haven't pulled the trigger yet - still looking at different paths. 

So this really isn't a 1031 question so much of a trigger of deemed sale question.  

And personally I cannot pull the trigger on a turnkey operator.

I would like to learn more before I pull the trigger in the next 6 months.