Insurance companies have become very nit-picky.

If you plan on only paying a portion of the private note off at refinance, you will want to make sure you do not record the note on title. 

I'd like to continue house hacking, but because I'm a real estate agent on 1099, I need a solid plan to generate more income to help with qualification.

Yes so that’s my plan I wanna get into fix and flips to gain capital.

My plan is to refinance the land with hard money, pay off my debt (40k) with the cash and then take over my rental property.

My insurance didn't cover his items.

Moving forward, a better alternative than hassling yourself and your guests with damage deposits is to just purchase damage insurance through a company called Safely for each booking.

Basically if the interest, taxes and insurance (ITI) is equal to rents it qualifies instead of having to qualify rents against a full PITI (principal, Interest, taxes & Insurance).There are also some DSCR options that can use the STR like VRBO which tend to be much higher then the LTR - long term rents.

Doing your homework, checking everything carefully, and planning well can help you avoid big mistakes.The best place to put your money depends on things like how the market is doing, what's happening in the economy, what you want to achieve, how much risk you can handle, and what you like.

Up to $69k annually double that with a spouseIf you have no plans on maintaining self employment activity and would rather go more passive then the SDIRA might make more sense.