I wouldn't necessarily recommend that a family with 3 kiddos go out an buy an STR but since you already own it and have it furnished, its a pretty easy trial.

It's a low barrier to entry and a good option for you, I would highly and I mean highly recommend you focus on location.

To close the loop on this story, we hired Rick Dempsey (who was fantastic by the way, highly recommended if anyone needs a MA-base SE...Matt Kelly, we really appreciate that referral!).

I have a few I can recommend.

Rare do I hear of recommendations but I do hear people asking.I would think in any big city you think about, a visit to a local NARPEM meeting or 2-3 visits would be a great idea. 

I would recommend reaching out to @Denver McClure as he may be able to help with a non-conventional loan

If you're still looking to connect with some real estate professionals in Pittsburgh to help build your portfolio, I strongly recommend reaching out to @Elise Bickel Tauber

Quote from @Sunil Ghosal: Would not recommend the East TN region to anyone right now.

Account ClosedI recommend that have a consultation with your tax accountant and/or financial advisor on ways to reduce your taxes. 

I'm obviously biased, but I think working with a broker will speed up your learning curve.If the broker you work with isn't transparent on everything they do with you (not for you), I recommend finding another broker.