Like others have said, I think this is a great time to reflect back to your goals and assess your situation relative to those.

I guess my thoughts would be:1) The chicagoland area and illinois has super high taxes (3 to 4% of the assessed in most of the chicagoland suburbs).  

It is a very risky game to guess loan balances as banks will assess some hefty fees for things such as "property preservation", I have seen as much as $70,000.00 of ridiculous fees like these in my experience.

After re-assessing, I went back, found what I felt would be the best suit for my personal style of real estate investing and decided to FOCUS - Follow that One Course Until Successful.  

Either the HOA goes up, there will be a special assessment, or it starts to turn ghetto because the HOA can't impose or collect the needed fees.  

Do they also assess credit and debt to income ratio like a conventional loan?

Many ways to make money in real estate and you probably just need to assess where your skills are at.

.- difficult for me to assess the accuracy of these claims.My dilemma is obvious and I am sure many of you have faced similar:1.

Going by assessed value (the tax value) is not necessarily a good indicator. 

If you're wanting to flip properties, I'd suggest getting in with a local real estate agent or appraiser and gain as much local knowledge as you can in order to assess your market area well.