Most really experienced agents of +10 years are degenerate gambling drunks and shouldn’t be trusted.

Our general model for investing at this moment is primarily urban core because there's limited supply for the folks who want to live there, whereas there are tons and tons of new construction all over the Jax suburbs...making it a bit more of a gamble imo. 

-Now surely this cycle will ride itself out over the longer term but for those looking to acquire property in the now and plan on a value add component,  its almost gambling on the future refinance...not the position most are comfortable being in with millions of dollars involved.I have been running properties through the syndicated deal analyzer and other DSCR spreadsheets only to find inadequate COC, cash flow, AAR, you name it! 

Some tenants don't care, they will take the gamble.

This is a bigger gamble but I think it has a chance for a big pay off.

Tesla was a gamble since I wanted a CyberTruck and it ended making me 1048% sold on September 2 when I sold I can buy it back after the first of the year a little cheaper and if the stock does well I can pay for a car. if not I buy a cheaper used one.

That's called speculation or gambling, particularly when the market has been growing for ten years straight.Sell the property and invest in something that cash flows today.

I am afraid of both possibilities as they can be a gamble of sorts one way or another but I am more inclined to make a claim with Citizens and see what I get. , without affecting my tenants (and income) as much as possible.

Gambling on the market crashing and home prices going down is just that, gambling.

@Philip L. you can do a land contract - you just have to gamble the lender isn't going to find out and call the Note due for violating due on sale clause.Don't recommend a LC to an occupant buyer due to Dodd-Frank regulations.