Siamese twin row home deal help

[Jack Clough]

Hi BP folks - somewhat newbie investor and closeted Realtor. I have one commercial property owned and on a 3 year lease. Looking to purchase another and here is where I'd like help. There are two commercial properties next to each other on a street of commercial row homes. They have been connected on the inside through the walls in the front and back on both levels and the basement. Current tenant is paying well below market rent (like 75% below). There are 16 parking spaces in back which could rent for $40/mo each. Seller (estate) is trying to sell the properties as a package. Each property was appraised last year for more than the list, so the seller got the not so bright idea of raising the price despite getting no offers. Then seller got.... no offers. Finally seller has lowered the price back down to where it's original. So, all that said, I'm looking for help on ideas to get it under contract.

Condition of properties: It is an old building and they need some work and new systems. Could be a 50% gut on each side.

Getting it under contract: I could just place an offer, but I want to be more strategic than that and have a better chance then just "hit and hope" (golf saying). I'm honestly not sure if the seller will reject anything below listing price, but let's assume that 75% of list is acceptable.

Offer: 75% of list for each property in total (but only 50% of list on the 1st property). Yes, on inspection contingencies as I think I can squeeze more out of them due to some water damage and some other issues. Settlement on the 2nd property will be contingent on the rehab, appraisal, and refinancing of the 1st property which may be 6 months or more later. I'll say this is partly due to the process and cost of separating the two properties. But I won't fully separate the two properties in hopes that the contract on the 2nd property stays alive (which I think it will because we'll be paying the barely below the list price for that one). I know, probably over thinking this one which is why I'd appreciate some honest feedback from the BP community. Thanks in advance!