Eventually I will scan the older stuff and dispose of the paper copies. 

At the end of the day, I find it better to be in a position where I can hold someone accountable for breaking my stuff than being a middle man between two tenants fighting over what one tenant did to another's stuff in the common area.This strategy is lucrative though, and I have seen many investors choose that method where I am based out of in San Diego.

Stuff can get very dicey when buying distressed properties with tenants living there.

But if you want to get your asset paid off and maybe paid off before things like the roof and other stuff wears out, maybe the 15 year would be the better route. 2) Do you want to put extra towards your mortgage ever to save on interest for these homes or do you put all that money towards getting more homes? 

Stuff happens. 😀 I called and settled now.

What are some creative ways that I can still do the owner financing and he can still get his car stuff?

As long as I'm the only one buying stuff, Excel is fine, and I find it easier to categorize stuff and navigate quickly. 

I use spearhead insurance,theyll do LLC's and stuff in your name. good prices on umbrella policies as well

Floor and Decor sells this stuff called Mapei Eco Prim grip that you can paint over pretty much anything.

If you used a 1031x to purchase the property, then you won't qualify, even if you used it as a primary residence.As for the $1.5-$1.8M range, those are rough numbers, but let's say you list and sell your condo at $500K, and then let's conservatively say $50K for closing costs (6% commissions + other stuff; this likely high).