Why would I be cash flow negative and losing money for years and years?"

I was scared of actually getting the deal done as much as I was to losing the deal.

I was losing money every month and was done managing the property.

It’s a lose-lose scenario.The only real winners are the lawyers and politicians.

You can not lose anything and no one can take from you.  

I would like to park my license somewhere so I don't lose it.

If you have high W2 income, the amount your STR makes (or loses) will be peanuts compared to the tax savings.

.* Automate Follow-Ups to Stay Top-of-MindMost wholesalers lose deals because they don’t follow up consistently.

You lose all of the control and these are long term investments - but in my experience the returns match what I had on the active real estate and I am hiring professionals to manage the assets.  

It's not only the money you'll lose, it's the time you spend (I figure worth $100 hr) and the mental anguish and stress.