I haven't taken it, but would assume it was at or near their best stuff...the inability to ask the specific questions you had might have taken a part in that.  

Because you can assume no Section 8 tenant has good credit, my leasing decisions had more to do with meeting each tenant myself to get a gut feeling based on their communicativeness, timeliness to showing, what questions they asked, whether they looked me in the eyes or avoided eye contact, etc.The downside of section 8 was the annual, then bi-annual, inspections. 

According to the Planning Board, the intent of the RM-2 Zone is to create, maintain, and enhance residential areas characterized by a mix of single family homes, duplexes, townhouses, small multi-unit buildings, and neighborhood businesses where appropriate.I'm assuming by definition I am zoned to convert to a triplex?

ok. still worth considering ASSUMING it's legit. 

Assuming the area checks out, I’d rather buy in a high price area that has little to no cash flow rather than an area that has cash flow but lower price.  

If not, you assume the risk and all potential consequences attached.

Early 2017 investment, assumable, high 3s fixed-rate debt with a 5-7 year expected hold period.

You owe two taxes:A. capital gain tax on $150k ($500k sale - $350k purchase)  PLUSB. depreciation recapture on $100k of depreciation taken.Now, let's assume that you messed up somewhere along the way, and you only took $70k worth of depreciation instead of $100k.

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

Also, I am assuming since you house hacked that you only did 5% down, which then increases your mortgage payments compared to 25% down buyers.