It is very much case-by-case and requires understanding of the current tax regime for personal itemized deductions, as well as gambling on the proposed changes to this regime by the next administration.

I self-manage, but I understand that's not a practical option for most people.

It's a tough part of STRs that some investors struggle to understand, but lending off residential assets based off how much the home can earn as an STR is far too risky. 

We managed to navigate it, but it was a lesson in the importance of understanding both federal and state regulations.Given your location in Boston, Massachusetts, it's especially pertinent to consult with a qualified intermediary or tax professional familiar with both federal and Massachusetts state laws to ensure a smooth exchange process.

I do understand that market value becomes what has been paid for a deal but with minimal work and renovations my deals almost always significantly increase in value in the first 6 months.

Having a clear understanding of these will help you avoid costly mistakes.

I understand as someone new to real estate investing there is a lot to learn and even though I have read many books, until I do it myself for a few years, I will be far from an expert.

New to real estate but possess a deep understanding of the responsibilities to continue to gain knowledge and remain loyal with my clients and professionally with my colleagues.  

@Jamie BanksI understand there are multiple parties: 1) displaced insurance policy holder (tenants)  2) ALE 3) The company that supplies all the furniture and install the washer and dryer. 

@Elliot Rosen, do you understand the issue?