Even the best tenants will not treat the property as well as you would and if you invest a large amount of money putting in high end finishes, you may be disappointed upon move out of that first renter.

I work mainly in major markets and can tell you that the larger banks on large multi-family deals like to see at least 2 years seasoning before they will offer a cash-out refi.

One of the very large boilers is pretty old (other pretty new) but the building itself appears in good shape (had a fire 2009 but renovated). 

If you make a mistake you could end up in second position with a large debt ahead of you.

I just needed to know a good company to call to get a ballpark on what a small, medium, and large remediation would cost.

My guess, some will, some won't at which time you can give the poor payers the 30 days notices (essentially giving them a probationary period with the month to month and new rules to see which tenants can handle the new format and which can't ). 

Detached one car garage, large basement for storage and laundry (also new).

With a large downpayment, it will be much easier for you to secure financing.  

Does he have a large investor base willing to dole out gold like that??

It would be a wonderful world if everyone could afford every safety device and had time to research them, but the truth is that sometimes you have to wait until time and money permit you to set up things for a large company.