I’m not sure when to decide that I “know enough” to make this kind of investment, or if I should continue educating myself before pulling the trigger on a property. 

They rolled over on a deal that was pretty cut and dry in my opinion, and really let me and my client down after months of dredging through paperwork and underwriting. 

Rents will go up and your biggest mistake was to buy a nice house in a desirable neighborhood.The real threat is buying in the hood, leveraged up to the gills, maybe even with hard money, tenants are bleeding you dry, while you are writing checks to attorneys and contractors.Milwaukee is getting a lot of attention lately: cash flow is still better than most places and appreciation is stable at 5-8%.

@Cody M.I would add a Phase I Environmental Site Assessment as a contingency to any offers on properties more susceptible to environmental issues (dry cleaners, gas stations, auto repair garages, etc.)

The basement is dry as hell, and it's nicely decorated.QUESTION:  What types of financing, financial assistance and tax benefits does one get from being a registered landmark in a historical district? 

How do folks make the ceiling dry and fix it?

Your management has to be top notch, your marketing has to be top notch, your pricing has to constantly change with the environment, your design has to be incredible and the photos have to trigger that booking response.

I have not pulled the trigger yet on a second property due to risk averseness, lack of capital and analysis paralysis.

(Fannie/Freddie allow you to transfer into an LLC without triggering a "due upon sale" clause, but ownership of the LLC needs to match the existing title of the property). 

Compared to  CA AZ NV OR WA which is very cut and dry..