He's still a loose cannon.I am willing to eat crow on the boring company. 

Condo's usually have high HOA dues which will eat into your cash flow.

Early on in my career, I saw a close frend do something similar.. she borrowed from her circle to finance a rural fixer-upper, then paid them back once she refinanced after the rehab.I’m guessing that massive yard plus the barn is already a big selling point for your tenant, especially with a family that wants a little extra room for animals.

Easy check-in, check-out, no frills, I'm going to eat out anyway. 

There are opportunities out there but some strategies are risky. 1 - Airbnb (STR) comes to mind - very competitive, very saturated and becoming highly regulated.2 - Most STRs are transitioning to MTR so that market will be saturated soon if it isn't already.3 - Insurance crisis in florida is getting bad so those costs will eat up cashflow and short term appreciation.

We eat the first one, thy get a picture of all the glory the plumber pulled out and the second time they get billed.

If it's a good asset(meaning primarily good location), you eat the 5.3% cap no problem you own the physical asset.

Before renovations, the property isn’t cash-flowing enough to justify a $360,000 price tag, especially if financing eats into potential profits.

Those things eat your introvertness & lack of sales background for lunch.

I was hoping to hear some ideas on what everyone is doing, other than working a W2 and eating ramen.OP to respond to this post versus your original.