Talk with your lender about this proposal...  1) Get a solid quote on the roof replacement and share it with your lender.    2) Put the funds in escrow with your bank for the sole purpose of replacing the roof.    3) Close on the property.    4) Install the roof.    5) Get reimbursed for roof expense out of escrow.Most banks are fine with something like this if they know their downside is covered.  

Frame and finish a L shaped wall in the current recreation room wall approx 7' long x ~18" deep.B.Remove door to "office" and open wall to frame out closet, or just close off.C.Remove wall separating bedroom and office (wall is ~7.9 long)D, F, G Close off 3 interior doorsE.

I am doing this completely remotely, which has been a massive pain/lesson learned (topic for another day).I signed a very high-level agreement (i.e. expectations simply say "drywall and paint") with him for drywall and paint work at my home for a total of $10KI have paid $5K as a down payment as well as ~$2K in materials over time, as neededThere have been multiple break-in's in the home, and he has done me favors of working with the police, and boarding things up.

Feel like we shouldn't be losing in property nowadays. 

It sounds like to need to get rid of this tenant.

Hey Weston, I live and invest in Columbus as well.

It seems like we could get a down payment for a new, cheaper property and some passive income while also saving the buyer money. 

I've heard of instances where I've seen the investor do well long-term and some where the investor has been able to build and sell or just hold and eventually sell if new developments are coming up in the surrounding area. 

I agree as well. 

Yep seen them as well.