Most recently we’ve also seen a lot of outside investors move in because of how the market has been performing, especially on the multi-family side of things.

This is where you tell the seller, if the guy you find can't perform, the seller is SOL.

performing real estate related tasks.

I thought the Owner's Policy only covered the buyer's portion of the home, ie 25%, so I am confused as to why it is more expensive.I also don't understand why there are two separate policies, presumably when there is only one title search performed.

You definitely want to perform a more detailed analysis before moving forward.

My lender lumps all my debt together, including rental property, and then performs a DTI using 80% (I recall) of the revenue generated from my rental income and inculudes that as regular income.

I projected a 21 % leveraged cash on cash return but in reality it has been performing much higher.

Alan I would google Ray Alcorn's article on performing due diligence on commercial properties (applies to residential as well) and investigate this deal (and all others) thoroughly.

He's gonna perform a load calculation, take a look at the support to see if it's exhibiting any stress and then tell you that it's been functioning for 113 years and will probably continue to function for years to come.

I would be willing to bet that if you worked with the tenants that want to stay you would be able to get in the unit with their cooperation and paint or perform some other improvements along with what you mentioned.