I am meeting with banks and some local connections I have with real estate agents to start getting a feel on my position financially as well as get a feel for the local market.

However, the landlord may take the tenant to court based on non-payment of rent increase, if this happens, the tenant may argue to the judge that the increase is unconscionable.

Given how hostile housing courts are to landlords, that's not the hill you want to die on.If you really want to pursue this - and it may not be worth your time - I think your next step is to go to small claims court.Filing is easy. 

I'm a strong believer in keeping your people first and while the goal is to be able to have financial freedom so that I can travel around the world, I want to be able to make sure that I take care of home first and give back.I found a meetup in the next couple weeks actually and I am so excited to attend and network!

Offer your services as a financial analyst on a consulting basis. 

Get a rentroll, leases and financials and have an inspection done by a licensed inspector.

The $1,000 a month is a bit much though unless he does EVERYTHING, including leases, turnovers, evictions/court, lawn care, etc.

I have made my share of mistakes and they can be mentally draining and financially painful. 

I am a born and breed Rhode Islander, currently working as a Marketing Manager with strong ambitions to be financially free before I am 35 (currently 26).

You need to decide what marketing methods you want to employ given time and financial constraints.