You want to be mentally and financially ready for your first purchase here before moving forward, regardless of whats going on in the Real Estate market.

I used to do my own taxes but eventually you need to get out of the do it yourself mentality in order to grow your business.

I would LTR it and have the set it and forget it mentality, and look into getting a LOC on the 100k and finding another investment.So I would do Option 1 & 3ish assuming I like the property.

IDK if they will be happy someone wants to give them money for their house, or they are of the mentality after everything they been through they want their family's to hold on to it?

Decision Fatigue: Analyzing properties, financing options, and market trends requires mental effort.

Personal use includes: storing of some family personal papers/records which I don’t want to keep at SFH1, sometimes I have a guest over who I don’t want to live with us, sometimes I need to sleep at SFH2 when I am working late at my job/taking a mental time out with my partner.

Initially, I was thinking with a mom and pop mentality, but now I understand how to professionally structure funding from family and friends and make it legit.

Drives my wife nuts since her dad has always been a do-it-yourselfer and doesn't understand my mentality.  

Further, much to what I have already said, the real practical matter is it is dangerous for investors to have this type of mentality.  

The people here are very valuable assets, if you have a student mentality then you will learn an awful lot here!