I have a few that I've seen, this weekYou'd need cash, though.I reasonably commonly see subject-2 purchases for $50k or so, that cash flow and have equity. 

Being in the services will complicate your plans to hold and for that reason your best option at your age may be to buy, add sweat equity and sell when transferred.

He would need a licence and will never qualfy for health reasons.

Although I currently reside in Southern California, I’m looking into long distance investing in Wisconsin, because the market is more reasonable for me, and that’s where I plan on living in a couple of years.

What would be a reasonable return on a wholesale deal.I would potentialy wholesale it to my real estate agent and they would put the $15k in for repairs and they would list it.

For that reason, Chicago will not be my choice. 

This is for no real reason apart from:1.I applied for 2 business credit cards, one with my local bank and one with Amex.

If the area is safe and reasonable distance from Boston, i'd consider it. 

Revealing other offers weakens my seller's position not only for the reason you outlined, but also because it lessens the chance to stoke a bidding war.

A good lesson is to never sign off on a change order unless it has been discussed, shown to you, and you and he agree it is extra and the price is reasonable.