Jon,
Thank you for your very thoughful reply. At this point, I'm probably going to pass on the deal unless I can get it at a much lower price. I suspect I could make it work if the price were closer to 1.5m but I doubt the owner would consider selling at that price.
I've walked through the property and can tell the owner has definitely not put much in to the building over the past few years. Latest major expense was a new roof a few years ago. The heating system is servicable but really needs to be upgraded/replaced. The apartments are in decent condition
There is some room to raise the rents but I think the revenue from that would be offset by improvements needed to the building.
The theatre space used to operate as a 5 screen movie house but is way below today's standards. Its only hope for seeing use again is to return it to its original use as a live theatre space. Easier said than done I know. I have worked in and run many performing arts buildings in my career. It is a very tough business to survive in.
Personally, I don't see anyone making a play for this property. Me, I'm a theatre person and would dearly love to see this gem of a theatre resurrected. I can't do that if the cash flow is negative though.
If I could somehow wrangle the price down to 1.5m and assumed the operating expenses were closer to 45-50%, I think that would work, no?