You would suggest that I maybe buy first a multi-family with a few units to start and possibly live in one to start?

I live in San Diego, CA and purchased 3 single family homes over the last year, 1 in TX and 2 in OH.

My wife and I bought a single family house in Texas a few years ago.

Quote from @Raghavendra Jakkani: I have a single family house available for rent.

I was debating if I should partner with a friend or family member who is willing to work on a property together. ill be sure to make sure things are done legally and fairly so no one get short sighted and things don't get messy.

My single family home is rented, but I got lucky getting the bare end of good interest rates, and I made sure rents would cover mortgage upon leaving.  

That was a great move for our family what a place to live in the 90s..

I moved to Ohio and now work as an agent and a new investor in the Cleveland market.Single families are in the 90-120k price range, and duplexes are in the 120-180k price range.Many out-of-state investors have grown their portfolios in Cleveland using the BRRR strategy.

Your lease purchase arrangement would be good as long as the senior or their family have enough money for assisted living care until you execute the purchase. 

Investment Info:Single-family residence buy & hold investment.