If your system is bad, you are talking BIG money to fix ($15-20K in my area). 

This is because state law is not favorable to developers of condos and those developers have been burned so badly these laws that they can profit more and have better tax advantages by building "condos" renting them for a decade and then selling them as condo's 10 years later. 

It's too bad you had to foreclose on the first buyer, what were the costs to take it from loss mit thru foreclosure?

If you are looking for forced savings of $900/mo, this may not be a bad option as you are probably paying down equity pretty quickly. 

Well if that small loan is in a bad area that can't sell, and big loan is in a great area, and the buyer got it at a steal, then it's not the case.You won't get many lending offers on low cost deals except for one company down in Philly, who doesn't mind taking over your property...

A good deal of it is cosmetic but as its an older building and the current tenants (month to month thankfully) are treating the place like the slum the current owner has let it turn into, there are plenty of less cosmetic fixes that will need to happen. 

@Jonathan Taylor Smith not a bad idea, but from what I understand he does not want an entity because he doesn't want to report to the IRS every 3 months, hes using an accountant, details I'm not sure.

I have found a huge difference in the way I am treating as an investor depending on the bank that I use.  

An umbrella policy is not a bad gap filler either.

Being conservative isn't bad thing (especially you're newer), but you want to be conservative and accurate at the same time.