Hi guys, I've recently moved to Indy a couple months ago and I'm looking to get back on the investing saddle.  

Really worry about not clearing up credit and being saddled with potentially bad/contingency terms. 

No reason to saddle both of us with credit if not necessary!

It is not uncommon to find a pharmacist saddled with $400k of debt out of school.

These are giant steps you are looking to take in an initial foray into multi-million/multifamily acquisitions.It's not impossible, but, you are saddled with long odds in achieving your goal in my estimation.

We got back in the saddle and started up again, but only 1 weekend day at first.

That is an enormous red flag.If that is normal in Detroit, then that means your tenants will be able to easily jump ship and find a place that will be cheaper if you saddle them with utilities all of a sudden.

Many small businesses fail becuase they lack focus as the entrepreneur is saddled with activity instead on focusing on productivity (my over simplified recap).

As I type this the more reasonable it seams and I see they saddled it properly.  

That extra few years of schooling will earn you so much more money over your career.Sadly many just go for bachelor degrees which are worthless in many cases.Almost all these applicants will have bachelor degrees.The paper won't get you the job it will be how you present and sell yourself and networking skills.So certain fields it pays to have a degree.Most don't know what they want in college and get a Bachelor of Business degree etc. that covers many jobs.Most of these students are saddled with MASSIVE student debt and oh by the way the student loans are relentless in recovery and cannot be discharged in a bankruptcy.The government WANTS their money.I might go back to college someday just to graduate but I don't know.Probably years later when I retire.