So, my question is still what are somethings to take in to account when choosing a cash flow market long term?

Whatever avenue he chooses, I definitely recommend NOT using all his cash on one deal. 

I have had tenants choose the month-to-month rate and stay for years paying more every year.

@Nadia DaggettYou get to choose your appraiser?

The only way to answer this question definitively is to calculate your return for each scenario then choose the way that gives the best results.

You may also choose blanket insurance.

However, the OT won't be unlimited forever, so as of now I'm getting as much in as I can and build up my bank account which in return will set myself up for a better scenario when I do choose to start investing in real estate.  

I would choose to mortgage the property to the maximum and not pay it down, When equity builds keep pulling out the equity to reinvest.

You as an investor, especially in a sandwich lease may choose to record your memorandum of option or other similar document to protect your interest and potential equity in the property, but you're unlikely to record the option with your tenant buyer. 

I, too, have been contemplating about getting my real estate license only because I recently have a newborn child and would like to earn a little money on the side and use that commission for other investments while learning more about the market.Good luck with whatever decision you choose and I look forward to hearing other suggestions and pros and cons from other investors!