With few other similar properties on market at time, I opted to bring cash to close and reminded myself to get better references for a more qualified (smart/honest) lender in the future.As my dad would say, many would like to have those kind of problems.  

Planning a more concerted effort that isn't creepy or annoying.

I'm not sure if there's a more creative and beneficial way to interpret it for tax purposes.

I would recommend reaching out to local professionals to get a more in-depth feel of the city.

A more established city like Chicago has multifamily properties everywhere, so you can actually house hack in areas where you don't mind living.

I think this would be the best first step to get a more accurate sense of what you're actually potentially in it for. 

Like most have mentioned already, multi-family tends to be a more recommended and popular strategy especially within most of MA.

HOWEVER, if my rental was in a more competitive, less desirable, area, I would allow pets, with an additional pet deposit. 

If there’s ever a more significant expense, I can always contribute money back into the account to pay for it.

Either of these skills takes time to learn, but the latter has a more limited downside and thus does not offer the upstroke either.