I already invested in 2 properties the traditional way (conventional loans) but am realizing that money is always going to be an issue.

What tenants don't realize is that they have a huge incentive to cooperate.

Not all syndicators are similar, there are some that take on huge risks and they might not even realize it because for almost 10 years you could buy poorly and the rapid appreciation bailed you out, going forward they might not be able to repeat what worked before.  

I realized the grass wasn't greener, and I ended up building back in the Chicago area once again.

Posting the same question in multiple forums.After reading through, I learnt the lessons and applied it as regards questions I would normally ask about my interest in wholesaling as a strategy to starting in the Real Estate Industry, I realize a whole lot of persons had same questions and I learnt from the Responses on the various discussions.It also changed my perspective in the way I approached the vets in the house, right now I just want to connect, I mean we are seeking financial freedom and for most of us that is time to do what we want and if I don't have regards for your time by being valuable to you, then I don't regard you enough.

My brother and I self manage 12 units (I realize this is not our best use of time).

He did recoupe what he invested luckily but I suddenly realized their system relies on the buy ins of both parties which means if you have to deal with shady contractors, thats just how its going to be.

I realized that one of the things that I would need to do to many of the properties that have peaked my interest is convert a living space into a kitchen.

Look at it from both a pure cash flow perspective (since you'll be realizing your gain) and a return on equity perspective.

There is also one big issue with your tax projection - the taxes of $280 are based on the vacant land taxes and will likely go up to ~$2000-$3000 in a year or so when the assessor catches up with you.I realize there is a 1031 involved so a real estate purchase is necessary, but you should compare your ROI to a safe yielding instrument like a 10 year T-note or AAA corporate bond yield.