This is all we have.Am I missing something more simple and obvious? 

Indianapolis & Philadelphia have properties ripe for the picking right now for rentals, and appreciation in those areas may be substantial in the near future.Good luck

I knew the building and immediately picked it up.

Is there any other way to go around this or do I have to pick up a second part time job just to look good to the underwriter?

Having said that, your gut feeling may have picked up something subconsciously and a lot of the time that little voice is right (see Malcolm Gladwell's Book - Blink). 

There is a rural property in the Kansas City area that I have an interest in wanting to buy, and I’d like to pick you all’s creative minds to help find a way obtain it with the lowest risk possible.

Doing everything in an LLC at first (normal LLC, not LLC taxed as an S-Corp) will keep things simple when you start, but make sure you get advice from someone who knows your exact situation.I would recommend having a conversation with your Real Estate savvy CPA BEFORE you do anything.

I quickly realized picking individual stocks wasn’t my thing.

Also, he can actually call IRS and get his copy of 1098 directly (Wage and Income transcript) from IRS if absolutely needed, It is a very simple process. 

I admire the fact that you work with under privileged kids..and the fact that you are not afraid to pick up a paint brush.