As Craig said, I would check out the person's social media accounts and look for red flags.

Loose doorknobs and faucets add up.For Multi-families in Boston and Cambridge, I view an inspection contingency as a red flag.

My goal and plan is to find a deal that is smokin hot, red hot and find out if being a landlord is something I want to do long term. 

I myself own a 4600 sq. ft. house on 20 acres in Redding CA and have rented the rooms to students at a local ministry school, a Christian missionary group, and currently rent to a sober living home, that subleases the rooms to women in transition. 

Also a home office is NOT a red flag like it used to be, because so many people work from home today. 

It's red and white on the app store if not!

I'm at the Salt Lick in the back right with a red backpack if anyone else is here. 

Are these red flags?

So that's what I would focus on, along with giving the front of the house a little sparkle (first impressions and all). 

Buy and Hold real estate investing is a lot like the game Monopoly... you start out with the little green houses and eventually move up to the big red hotels.Same goes in real life.