I think there are two maybe 3 ways to look at this in my mind.  1) you go into it and bring it all up to modern standards but using that old charm to basically take what is there bring it up to modern standards and rent it out essentially I'm thinking cocktail bar or something trendy like that.2) most banks are on really good centrally located real estate if this is true, then I'd consider it for the dirt, plan to scrape the lot and go vertical with whatever the highest and best use is.3) a kind of combo of the two, if the lot is in a good location and its doable, pull the vaults or other "character pieces" out of the building, scrape the lot, and build whatever is best suited for the site there, but incorporate those historical pieces into the final designs.Is the site near a major retail area? 

@Shwetha Pindikuri,Assuming an FHA loan with a second mortgage can be tricky, but it’s definitely doable with the right lender.

I can see a re-roof or mechanical upgrades pushing that number higher than normal for a couple of years if he was making improvements to the property.On the utilities were any of those 13 units not paying utilities before but now are where again you could see if the lender will back them out as they are no longer an on going expense even though they were included before.It might not get you where you need to be, but it could be a start to at least get the expenses back down to 60-65% so maybe it would be doable with your lender.

I'm not a tax expert and dont know how this would conflict with the tax deferred basis, but if doable, this isnt a bad option, either. 

One thing I will say is you can absolutely find great cash flowing deals in New Britain....Hartford may be a little tougher because of higher taxes but still doable.

A less than 5% vacancy is definitely doable even in a small market if you push it and run like a business and not just an investment.   

You have a great rate and a house that's getting too small, but upgrading to a larger home with a larger rate is not doable.

That being said, this is mainly doable for folks taking on cosmetic rehabs with great time management/construction management skills.

Thank you.If they’re in the same state, it should be doable in a portfolio loan.

Conversely, he could give me a hundred books on his business and I would be really, really sad to tell him I couldn't possibly read them because the topic is such a snooze.