Sixteen homes to inspect- roofs, hot water tanks, soft floors, siding damage, decks, porches, furnaces. 

My duplex - built 1989, 2,060 sf, 2 bed/bath, 1 year old roof, value if I subdivide (county already approved) and sell each separately $150k each ($300k total)Investor duplex - built 1995, 2,300 sf, 2 bed/bath, 5 year old roof, value around $310kThe investors initial request was for an equal trade and they would pay realtor fees, which I replied wouldn't be equal due to buying/selling costs (recording fees, title insurance, closing fee, survey, inspections, loan fees, 1031 fees, accountant fees, repairs), taxes would increase due to new sale price, I'd trade a 3.75% mortgage for a higher one, and I'm on the 10th year of a 30 year loan so resetting that to a new loan would restart amortization and pay more towards interest.

There are never full photos of the mechanicals and basement and roof line so you will never have even a bare inkling of what the potential repairs will be.

We currently have roof done and siding up. 

I did minor improvements to both of those, but unfortunately had to replace the roof on each (Flat roofs suck, lesson learned).

Lets say you needed $100k in financing at 12% + 2 points and it took you a year to rehab and refinance that is an extra $14k + closing costs.2. you mention roof is 18-20k.

I own a roofing company in Denver and a separate gutter company there too. 

It's what you paid, minus the value of the land, plus what you spent on long term repairs (roof, furnace, etc.

Estimated cost for remaining changes (all new electric, drywall, tile, fixtures, cabinets, roof, doors, windows, heat pump, some siding, and fencing.

Shed has collapsed roof.