@Kenneth Shelley   another way to put what Don mentioned is you may want to walk before you run.if at this point in your career your asking these very basic questions your not really qualified to lead your investment group.. you may make it ok but you could very easily go through a steep learning curve and lose your close friends money and based on my long career working with investors I can tell 1000% you lose their money in a RE deal and you are no longer friends no matter how close you think you are now.as for some constructive feedback here Is what I would consider if I was in your shoes.I would get my Real Estate license so you can prove to them your a professional and care about your craft..

Given my circumstance I have set my sights on a multi family to get my foot in the door get out of my rental and get some what I'm sure will be hard earned experience at REI.

If you lose a deal, oh well, life goes on.....

Just double check all those numbers... you win or lose when you buy!

I don't have the resources to buy sight unseen.

Geez, would a law professor be responsible for an attorney losing a case?

If those miles between home and job site are not considered business mileage I am going to lose a lot of business mileage deductions.

Now that I will be renting it out, and renting a place for myself somewhere else, how will the taxes play out, will I lose all the tax incentives from the mortgage?

I got my License in 2006, worked in the Default side of things, from my observation in the Fox Valley area (where i worked till November of 2014) values have not yet fully recovered to pre crash insanity numbers, we didnt lose sharply but are not returning quick either, while right now, activity is high, prices are not yet following, we are still down a good 10% I dont see that coming back any time soon, nor should it, prices were hyper inflated in 06/07' but who knows, with more buyers in the market that could change. 

Thank you for sharing John's web sight.