Leave it and invest in stocks?

I can also get solid, 7%+ returns with a couple of oil and gas companies and bet on rising energy prices, but I'm separating stocks, REITs, and notes from real assets that I'm purchasing.

This is true of the stock market as well as real estate.

Now to be clear he still has near ocean front rentals too and this is his part time gig...semi retired and the semi part is the 1000 miles away stock. 

Generally speaking your investor should want better than stock market returns on their capital outlay...which means more than 8%. 

The rest is wetland (including a man made fish stocked lake!)

I think one of the biggest advantages is they are in stock.

I'm not a huge stock market person myself and I prefer to limit my equity positions to 35-40% of my overall net worth.  

I have some stock market experience and have been able to do quite well, however the volatility is frustrating and it sounds like the possibility of higher returns is greater with real estate.

If I were to put the money in an investment such as a stock that I would expect to earn me say 6-8% (obv still risk to lose the principal), it is slightly different then my scenario where the investment such as the money for a refinance is gone right away and therefor would have to like you said "pay myself" back the principal first before anything beyond would be considered profit and therefore would obv have to also account for the time value of money since it would take even 1.5 years or so with a refi rate of $2800.