.- Im thinking of not charging security deposit because of all the strict MA laws and just using the last months rent as a sort of security deposit, thoughts?

Big thanks to @Zach Lemaster and his team at renttoretirement for making this seemingly complicated process with strict timelines a very easy process to navigate so I did not have to end up paying capital gains tax!!  

I'd also suspect that as an owner-occupant, one might be able to skirt strict STR laws, and rent out a primary in an extremely in-demand market, especially in the near-term (think collecting huge fees seasonally around CU football games the next few years). 

Yes you want to establish your credibility with a bank and they have very strict guidelines about what they will finance and what they won't.

These deadlines are strict, so it’s essential to plan accordingly.Good luck with your exchange!

for example, they will screen tenants according to strict criteria, and shield you from screening and placement issues.you should of course do whatever you want. 

Then use those funds strictly to make renovations keeping all receipts. 

Splitting this house isn't an option as our HOA is very strict about single FAMILY residency.Does anyone have advice?

We are strictly cash only and buy properties straight up.

Commercial lender got back to me and they will in fact issue me a loan strictly off my note.