Is it worth to pay that much for 1:1 coaching for 6 months and a laid-out course? 

Our tenants pay $2,700 in rent and the mortgage+fees comes out to $2,360.

If I sell one house per year, it will pay for itself.

Just sell and pay off that loan or two.

What should I do if my tenant isn't paying rent?""

Quote from @Sarp Ka: Quote from @Patrick Roberts: Am I understanding this correctly that youre expecting to get a $700k property for $500k because youre paying cash?

If your willing to do so, you can live in the casita and then rent out the main home and have your tenant pay the majority/all of the mortgage (depending on what type of deal you find obviously). 

This is a the perfect vehicle to use for short term like buying a  property with cash, then refinancing the property to pay the line of credit back in full, and use it again.   

The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.  

Pay your attorney and your CPA for a customized advice.