I've tried four different agencies over the years and they all failed miserably.

If the HOA is against it, they can make your life miserable.

It didn't hurt the overall profitability, but I would definitely be more mindful of this with future purchases.Lesson 3: Don't tear your whole house apart while living in it unless you want to feel slightly miserable.

Name your economic cycle, people played Eeyore's favorite tune "everything sucks, nothing works, it's all miserable, everything is bad....".   

It has decent cash flow, decent cap rate, and decent  coc-ROI, but it fails miserably on the 2% rule and the 50% rule.

There are a couple managers locally who are failing miserably at their jobs and there is a mass exodus of HOAs trying to escape but a wise manager will only scale as much as they can take on.

I currently live with my parents and am looking into getting my first duplex/triplex in the central Connecticut area, as I do not know where my next promotion to a Branch Manager will be yet (I want to make sure I buy somewhere that won't make my commute completely miserable time-wise). 

If it's a big increase, 20% or more, I wouldn't even bother trying to raise the current tenants because they either won't be able to afford it or they'll resent you for making their life miserable. 

Driven people who don't have an active purpose or pursuit tend to be miserable.

I would never let my clients do it and I know someone who tried and last I heard failed miserably.