Is just any "guru" or training adequate to keep people out of trouble.

I'll keep your other advice in mind.

Or, keep renting and put your money in other places to grow.

We've sold over two dozen coastal and luxury Oregon Coast STR's the past three years and our entire day is invested in keeping up with the rules and regulations regarding short term vacation rental usages.

You can do a cash out fixed equity line or second home loan towards the down payment of a new investment to keep your current terms intact.

If you rent to him and something goes wrong, you will lose the friend and you put yourself in a financial bind.I recommend you tell him you prefer keeping the friendship and business separated so you can remain friends.

"DSCR loans don't count against your DTI so keep house-hacking"This is just NOT true.  

So, when you think vacancy, keep in mind that YOU and the decisions you make can significantly affect the vacancy time. 

Need to get a better system here to keep on track of this.

My first house is a 3 family but keeping it as a 2 family right now .