Will depend on several factors like the type of property, type of tenants, your risk tolerance, other assets you own, your estate planning, laws where the property is located, etc.

However from my observations the squatter occupied properties tend to be in lower barrier markets and I wouldn't personally want to spend my time and effort trying to create value in such neighborhoods.

You've already lost, spending $220k in that area is not something you'll recoup.

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.

I will have to spend some time debating these as tenants can't afford these increases. 

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.

I still love what I do but I know that it is time for a change and am planning on a 7-10 year transition to not needing to work for a living.

If you plan on buying in your entity I would set it up prior to seeking any type of pre approval for financing.