Seriously,you need to find a local contractor or building inspector to show you all of the actual problems that need repairs.If the plumbing and electrical haven't been upgraded in 100 years,change it all out immediately before they fail in the middle of winter.Make sure your HVAC is excellent as well.That roof probably needs tending to as well.Then you need repainting,spray foam insulation,flooring,etc.What fixtures is your competition for renters using in their homes?

There are numerous academic studies that show valuations in the public markets tend to be a precursor for private market valuations.  

(Great for follow ups)Direct mail tends to work best when you send a campaign of 5-7 different pieces, 3-5 weeks apart from each other.

Lenders, like myself, are looking at amounts $ of equity on smaller deals. 10% down on a $800,000 buy is a nice slice of equity, but 10% down on a $40,000 house is not enough (in fact it might be less than the cost to foreclose on a defaulted loan).I personally don't do 100% financing ever, like most other lenders, because skin ($) in the game tends to equal loan performance.  

I tend to agree that AirBnb should actively pursue and address their platform use issues with the municipalities in the NYC marketplace to prevent incidents such as the example going viral and threatening their rental platform franchise in this marketplace as well as many others around the world.

They tend to frown upon such shenanigans.

Im wondering if we should put the house up for sale in the hope it shifts fairly quickly, or try and cover the nut on both property's until we can rent it out for enough to cover most of the mortgage in Richmond,keeping to the buy & hold strategy that we were starting to implement.

I tend to avoid fixing things that arent broke, but would have planned on electrical with a 100 amp service on 3 units, especially if its the old screw in breakers. 

Real estate investors tend to be solution finders and the art of every negotiation is about negotiating solutions that benefit both parties. 

If you buy a distressed property, even a SF, you are going to have to tend to deferred maintenance and CAP EX.