The request was accepted - so I sent an innocuous note trying to see if I could get the guy to respond. 

Good luck, whether you're able to tackle this guy or the next!

I think you have realized one of the issues and it is very good to tackle it. 

My general advice would be to get skilled at one aspect of this business and have some consistent revenue coming in before you try to tackle another type of real estate investing. 

@Mary Mitchell welcome and it seems you may already know a more than enough to tackle your goal!

Then I worked on improving and actively enforcing the rules and regulations: Trash all over the place, smoking in building, dumpster, parking at the property was just wild and even dangerous.Simultaneously I tackled deferred maintenance items.

This is spelled out in my lease as the ONLY way rent can be paid.Given your strategy, you just may end up with an empty building on January 1st (or, worse yet, some non-paying holdovers you need to evict) - not ideal timing as there are less people looking for apartments that time of year (at least here in the NE).If the above paragraph gives you pause, you could keep everyone as is, and tackle the unit with the rent farthest from market rent (or biggest PITA tenant) with a new lease and rental rate. 

It's a business that you don't want to tackle alone and test the water especially when dealing with other peoples money.

Sounds like you're tackling your first investment head-on.A few tips that may be helpful to you here on the BP website:You can set up keyword alerts so anytime someone posts about Oregon City or any of the specific markets you're evaluating, you'll be notified.

There are many different ways I could have tackled this property.