He needed drywall panel, paint, caulk, caulk gun, screws and few other things and at the end it ended up being another $100 bill on top of what we agreed on.

I have been told we would get a better experienced banker from up north but I'm a little gun shy now.

So why when I show it to potential investors is the response not as enthusiastic as I imagined it would be?

do not sell for 30k. im assuming you bought this property because the number worked and you planned on keeping for 5,10,20. stick to your guns. the hard part was jumping in and your past that. fix the roof when you need to and then you will never need to do it again. or sell in 5 years before you fix the roof and make the new owner pay for it or pay for half

Successful was by hand gun. this is / was ugly and it caused me to change my tactic to where I would no longer buy owner occ foreclosures. 

But, I don't want to jump the gun as long as you feel good about your rent free situation.  

I'm now living in MD where I bought a condo based on the fact that I can rent it out and it should cashflow when I move out (which probably won't be long), so I've at least also convinced myself that that's a good idea especially with the low interest rates right now.I also enthusiastically second Mitch's suggestion to consider house hacking with roommates (or if you happen to find something with an ADU or even a duplex that would definitely open so doors for you)Good luck - hope you find something that works!

I see it similar to gun control.

I have a pile of wood, nails, nail gun, saw,etc.. at the bank of the river.

I think he jumped the gun with getting a place in Indiana and anticipated being out already.