@Mike JacovelliIt depends on what role these people play in your life.

I also am playing around with the idea of making a 3rd bedroom in one or all of them if possible as they have a lot of wasted space . 

If we're going to be internally consistent, IMO the playing field has got to be leveled.To do that, you have two choices.If you hard cap everything at 43% (and can no longer sell your home to that FHA buyer utterly maxing themselves out at 56.4% DTI), I can point to some dozens of millions, or hundreds of millions, of American voter homeowners ("homevoters") who will not like the impact this has on their home values, unfortunately.

And you'd benefit yourself by going to play golf, fishing or take a quick vacation trip - to make sure personalities mesh and build friendships among the members.

For now, moving from LA is not an option.I know in LA it is very hard to generate positive cash flow, and it's mostly an appreciation play. 

Every now and then she'll bring up just how much of an inconvenience it can be (except when we have others to play Catan with). 

Found out a great property is listed as a Historical Site. What has worked for all the BP listeners in the past?What questions should I be asking?Tips or advice?

@Jonathan Tran after analyzing quite a few properties in this forum in quite a few states, I've seen a wide enough range of property taxes to believe that they play a significant part in whether a deal cash-flows or not. 

Painting - These are the first trouble areas I think of when looking to add value, but please if there are other aspects of the house that play a big role in increasing value, please let me know.  

Plus it's not a great play for long term rentals.