Either the operating costs are so high that it cannot make money in its current state (i.e. no insulation, old & inefficient heating system), there is a physical problem with the property, or another issue with title, etc.I would not be in any manner of a hurry to raise my offer as you will need every dime to breath new life into the old building if you do purchase it.

Has anyone tried insulating window inserts?

I'm a conservative investor, and I think that may have insulated me from some really tough breaks, but it has also meant that I've lost out on some home runs.

The crawlspace should also be vented (and the floor insulated).Good luck!

Some sellers just pass on these hot potatoes, having milked the property by keeping all the rents and not plowing much back into it...Then the exit strategy is to sell to someone who may not recognize all the deferred capital expenses.Some ideas for avoiding the hot potatoes (where everything is at or near the end of its useful like) might be looking at age (but it sounds like most listings are a bit older), so you might only look at those properties with updated major systems and components (HVAC, plumbing, roof, windows, insulation etc). 

Much would depend on the insulation in the place.And Deanna is correct; you anticipating your unit to cool to 72 degrees is unrealistic. 

This gets you a nice short term equity bump ... though it is not yet "realized" since you didn't sell but it will insulate you to a degree from any short term market fluctuations and will also help your cash flow since you are in it for less than you would otherwise be.

It was insulated at the same time.

Also, check for asbestos -in insulation, siding, old floor tile, etc.

So conduct business honestly and above board and you will insulate yourself from most LEGITIMATE issues that way.