Don't be afraid to negotiate, particularly if you have a lot of rentals.4.

Quote from @Ben Trageser: If you live in your short-term rental (STR) property in a future year after claiming depreciation, depreciation recapture does not occur immediately.

I handled our rental unit renovations, but they weren't huge and this seems an order of magnitude greater.  

I am starting to get Lynn section 8 folks calling, but I have not gone through the process with them to know how they are with rental amounts.Yes, the ones with sec8 are in Haverhill. 

You've done well with your Class A rental, generating $500/mo in cash flow, this adds up over time.

They will let you know what you can and can't do without a permit and what you are able to do yourself within the scopes of those permits.My concern is because this is a rental, if you do anything that is not to code and the tenant reports it, you will likely have some much bigger issues to deal with.Given you note this is major rehab, I tend to lean to hire most, if not all, out. 

I’m giving myself about 2-3 months to make the necessary repairs before listing as a rental.

for fix and rental projects or for fix and flips?

To help expedite the rental unit approval/inspection, you can also talk with your local housing provider that runs the Sec 8 program what basic items they look for and make sure you have those covered. 

I like the feeling of being close by to my rentals and managaging myself.