When you say 2,400 sq ft are you talking a 4 plex building or larger building replacing a section??

I'd like to do this option, but how much would a roof replacement cost?

@Brandon Turner The podcast have replaced music in my car.

How do u find and how do u replace contractors?  

But we stole the home because of its condition.)I replaced 18 windows & all the doors (the doors were in the same condition).

The problem here is contractors, for example window replacement guys from big boxes, will test and if positive your install price wtill go through the roof because they have to wear suits, tape off and sheet over everything, etc.3.

Due to lack of experience and knowledge of repairs and replacements I am afraid I underestimated all the stuff that I will have to fix.

Assuming you have a mortgage currently, refinancing will replace that with a new mortgage so you still have the same number of loans though your payments might be higher depending on whether you did a cashout refinance (thereby taking out a bigger loan than the current balance on your mortgage).

If you need to replace the roof do you walk away?

From the outside I can tell the roof is new (installed <6 months ago), the building needs to be painted (lots of peeling already), some window screens need to be replaced.