His rates are well below market, even for the small town he is in.

The underwriting is based primarily off of the property, not you as the borrower so the main factors evaluated are property value, DSCR ratio (cash flow), LTV, and FICO.Also, I am from Boston and know the area well.

They can help you navigate any potential tax pitfalls and ensure that your strategy maximizes your benefits.Overall, your plan is ambitious and well thought out, but it’s crucial to keep these factors in mind to ensure success.

Get informed.

They are using the entire rental, why not make them responsible for fixing/replacing your roof or HVAC as well?!?

Well done!

I am very new to all these ideas and have been watching the podcasts, youtubes and reading articles as well, trying to narrow down my options.

And when Google seeks to monetize it, I would bet we see similar fees.

BUT I know some business owners who do this on their own as well. 

I can go up to 80% LTV on cash-outs and can do non-warrantable condos as well.