Hi,
The seasoned writers from this forum make very valid points. However, there's in an additional point I'd like to bring out. While it is true that due-diligence and proper pricing should prevail, sometimes it is also valuable to NOT be too heavy-handed in getting the price to where you want it.
By this, I mean, there are times when it would be better to leave some of the price on the table and negotiate terms and conditions, rather than to beat a seller down on price (unless of course the building is in perfect condition and you're paying all cash). If this is not the case, and since many lenders want to know that you have "skin" in the game, you might consider these possble opportunities:
1) Once you've determined where you need to be on pricing, let the seller keep some of their asking price, in lieu of them paying for some of the repairs -- For one customer seeking a reduction in the price of a commercial site from $700K to $550 to cover half of the land development costs. When they rejected that, I suggested countering with their $700K price, but them paying $150K toward the cost -- to which they agreed.
2) If there is the possibility of the seller being flexible on terms if they can get their price (or closer to it) then this would make sense also, depending on what your exit strategy happens to be. Take for example the situation that you gave. If, in fact, he only paid $37K for the property and now is looking to pull out $870K, you might look at splitting the difference in price, but find out what he intends to do with the money. Since you said he's elderly and looking at retiring, you might ask him to finance a substantial portion of the purchase price with payments deferred and a simple-interest structure that is on par with what he'd get from the bank where he'd make the deposit. In other words, perhaps he'd be agreeable to having the interest accrue on the loan (no payments) for 1-5 years at 5-6% interest and then balloon. If you don't have to make payments on that part, this increases your cash flow. And assuming the building is in reasonably good shape and in a good area, you can pocket the cash flow while the building appreciates to pay off the accrual at a later refinance or sale. You both win!
That's just two possibilities. Hopefully, I've stimulated thoughts of some other possibilities.
Kelvin