If they have paid off property (especially if the investor is much older), they probably have a healthy stock portfolio as well :) Debt has worked for me, and I'm glad it works for you too!

I guess you could offer up your property OOS, not sure how an affected victim would get there, if they have financial means, they could fly there or drive there, if they still have their cars. 

Any guidance is appreciated and I know it's not tax nor financial advice, just your thoughts.

With the future being so uncertain I realized there was a need to do more than just rely on my job for financial security. 

To defer all of your gain, you'll want to trade up in value, replace all the debt (meaning new properties have at least $350,700 of debt), and not take any cash from the exchange (this is boot which = taxable gain).As for replacement property, it just has to be real property - meaning it can be commercial, STR, land, etc!

That's before you pay any debt service.To answer your question: No, it's generally not a good idea to lose a bunch of money every month.

I think it would be financial suicide to give up a 500k a year job that you know how to do and is secure to launch into thinking your going to replace it with rental income.. unless your sitting on 5 mil plus in  cash with no debt.

This could also hurt my debt ratios if I go to borrow on another investment somewhere like my plans for the STR.  

What doesn’t work today may work in the future.Another challenge with the traditional BRRRR model is the resulting high debt load often isn’t fully covered by rental income, especially in today’s high-rate environment.

A couple of things I like to tell my newbies-Owning a short-term rental property can offer significant financial benefits.