Investing in Real Estate is always a gamble and it's best to limit your risk by renting where you live instead of taking on too much risk too soon.

Therefore, i'm left wondering if I should devise terms with a family member that'd give them a decent return on their money, allow me to get in for a low down payment and a reasonable interest rate and afford me the time to look for a job, perhaps in a different field, that i'd enjoy more.... like real estate investing.

What I continue to enjoy about working with Federico is when I ask questions he gives me thorough and thoughtful responses (and still does). 

You could easily lose $50-$100k GAMBLING on a future price drop.

Per my numbers I figured it would break even every month but would be a great long term investment and also something I could enjoy when I wanted to go to the coast.

I've enjoyed this model more. 

I still work a lot and really enjoy it, but am the owner and don’t like saying that.

As i’ve grown in the business, asking for help and sharing my mistakes has become a lot easier - I think I’m enjoying the journey more now, rather than just trying to get to the destination.

Would you keep the property and just continue to rent it and enjoy the cashflow?

I enjoyed the one year I lived in Jackson ( Madison county) love those southern manners !!!