Obviously, there is a lot of nuance to to each situation but all else equal I'll invest.

HELP: not sure if it’s a waste of time, or should I focus on condos, what other numbers should I consider when looking at potential deals (I check PITI to be lower or equal the rent), what I need to know about the market I’m in?

Agree with @Dan Mackin - you'll almost certainly owe the superlien amount which is equal to 6 months worth of dues.You may or may not owe all or a portion of the rest of the amount based on date of filing, etc.Be prepared to find the HOA board completely unwilling to negotiate. 

The units are not metered separately, and all are charged utilities via an equal split averaged out over the past year's usage with a 50% markup.

Also like I said I’m new to REI so I’m sure their are others who are vital to me being successful..

This person will be vital to your success.

If they are VERY professional, they will have their processes in writing as verification that it is enforced equally and fairly by their entire staff. 6.

And equally important, do you have some reserves built, according to your risk tolerance level?

I am new to the Indianapolis area and equally new to Bigger Pockets and Real Estate Investment.

everything being equal I think its cheaper on tax's and the rental control that city of Portland put in. to look in the neighboring areas and outside Multnomah county..