Putting Together a Deal For Two Properties

[Ben Sears]

I'm looking at two properties owned by the same entity. They are located down the street from each other and are of similar size and construction. Both are listed for over comps for the location and I'm looking to put together a deal to purchase both for a total discount. 

House #1

2b, 1ba

576 sq ft.

List for $58k ($101/sq ft) (150 days on MLS)

Target purchase is $42k

Move in ready and currently rented. I would invest <$5k for some cosmetic updates. ARV is $47-$52k

House #2

2b, 1ba

722 sq ft.

List for $55k ($76/sq ft) (150 days on MLS)

Target purchase is $35k

Needs lots of TLC. Interior/exterior paint and siding work, windows and doors, complete kitchen, complete bathroom, some interior flooring. Approximately $15-20k in repairs. ARV $58-$62k

I've never approached a seller to make a package deal and would be interested in hearing from those that have done this. Tips, tricks, what has worked for you.