Flipping family properties?

[Sheree H.]

A direct relative has two houses they're willing to sell me to wet my feet on. They are not investors; because of family situations, they ended up owning two houses, and now they're looking to move to another home that their son owns.

Since I'm new to this, I'm pretty sure my ARV and rehab costs aren't going to be dead on, but I took comps from within the last 6 months, and I've been reading through J Scott's rehab spreadsheets since he's in GA and our house prices are in the same range.

House 1: Split level 3bd/2ba, wood exterior, built in 1977. Loan of 150k with no other encumberances.
ARV 90
Rehab ~50k? Old wood paneling. The windows are those long rectangular un-openable kinds; should we change them? Basement pump floods occasionally. Bathrooms will need full remodeling. Needs gutters. Everything needs updating.
Using JScott's formula, MPP=8k (!!)

House 2: Brick ranch 3bd/2ba, built in 1975, full finished basement with another 3bd/2ba. House is paid off.
ARV 150k
Rehab 30K. Needs gutters. 2 bathrooms and 1 shower need re-tiling. Everything needs updating.
MPP=80K

The two houses are back to back. House A on a busier street, House B in a quiet established neighborhood. House A is right down the street from a top elementary school, feeding into a top high school. They are not open to selling only one. I am considering buying House 1 subject-to. Fixing and selling House 1 is priority b/c of the subject-to; I'm still considering whether to sell or rent House 2.

Does 88K sound like the right price? Are there legal hurdles to selling two houses in one transaction to a relative?

A giant Thank You and all credits to J Scott!!