Sometimes I have to show clients the math for them to get comfortable with it. 

Once I get to a point that it is making enough per month that I feel comfortable taking money out of the business that would be when I get to the point that it is worth have a specialist assist me in all deductions, credits, and future items that will help me to transfer from a W2 to working for myself fully.

This gives much better diversification protection across geographies, asset types, strategies, investment subclasses etc. versus putting all the eggs into one basket.The downside is that it's not for everyone, and a person has to be comfortable with turning over control to someone else.

I'd love to shorten that for him a bit with REI or just make it a bit more comfortable when we get there. 

I highly regret not being further ahead of where I am currently financially to where I could provide more comfort to those I care about during their vulnerable times in their life.You see, wealth is not just about you.

From what I’ve heard, properties that emphasize tranquility.. like offering outdoor seating areas, fire pits, or even something as simple as a hammock.. tend to perform exceptionally well in remote settings.You’re spot on about STR policies in Johnson City versus Knoxville.

You have to walk home, and feel comfortable.

Just make sure you’re comfortable with the interest rate if going either route.  

@Grant Shipman, I will say, I have not explicitly seen anyone violate these rules (that I know of), but more commonly there are a lot of people who have comfort operating at the margins.I.e. compliance officers/attorneys that stop at the letter of the law may say: "investment manager X, you can advertise your company all you want.  

If he doesn't need the cash now, you could also negotiate a split you're comfortable with to get him the return you and he feel he should have at the point you refi when the balloon payment comes due.