I’m about to be 29 and I’m hoping this really takes effect in my life in my 40’s.

Start with the end in mind --- what would be the investor's exit strategy for this home? 

Real estate is not the stock market and it's called buy & hold and not buy & sell for a reason.I did sell a few properties about 10 years ago when I learned the hard way that going into cheaper neighborhoods was not the right strategy for me, so that was basically a strategy correction and it was necessary, but also costly both in terms of dollars and time.

I was hoping someone with some experience would be able to answer a few questions I have, such as: What kind of deal finding strategies are most efficient in areas like these?

Talking to others also gave me insight into different markets and strategies, which made it easier to figure out where I wanted to focus my efforts.A simple tip I’d give is to start small and grow gradually.

The deal is risky unless you know the market well, have experience executing this strategy, and have accounted for the quality of the asset and tenant. 

I want to know is it more cost effective or easier to purchase the property alone and put it in a mortgage in our name or purchase the LLC from him that holds the property within it.

I like this strategy and plan to continue. 

And do they care if I do rent by the room strategies?

The first thing I ask is why am I Buying the property.I always look at the exit strategy first, is it going to be a rental, a lease option sell, am I planning on living in it.