If that's not the case, though, you would be taking on significant risk of not being able to handle emergencies if when they occur, and all/most of your cashflow may be allocated to rebuilding reserves (in which case...is it really cashflowing?)

- how are you handling sewage?

In pennsylvania my attorney handled it and it took 30ish days.

But I would talk to an attorney that handles evictions locally and not do this on your own. 

At that consultation, you can lay out your scenario and ask specific questions about the law and how the attorney has handled such matters in the past.

Trying to figure out best way to handle this situation and would appreciate any feedback/input! 

I think it was Kiyosaki who said something along the lines of "find a team you trust, pay them well and let them do their job".Sound like in this case you don't fully trust this member of your team or their process... so I'd suggest finding one who you do trust fully (and then back away and let them handle it).

When I calculate it out, a lot of properties are really hard to make a good deal without really high rent (which the market can handle, but again, is hard on the locals).

@Terrance Curry why not find a local painter to handle the condo? 

Hello BP WorldI am a Realtor in VT and NH, and I'm focusing on growing my team of buyer agents to handle the workload that the mainstream MLS is generating for us in our extremely hot market.