@Connor Hibbs What is typically the max loan amount for someone with no experience?

No General Contractor wants to do a remodel with the residents still living there....they will charge you more (they probably will not show it, but the prices will be higher because of the huge PITA factor and increased liability)I would wait until you have completely moved out and then just give them the house empty and ready to roll.....But you can get a Scope Of Work going and start getting bids...even plans and permits if you're going that far...

A few months into the process they ghosted us and then when the owner resurfaced more than a month later she said she was no longer going to do PM.

There is no point where you've "made it."

She must also check with her mortgage lender and insurance provider to ensure no restrictions and update her insurance to cover the risks of short-term rentals.

I think that the red flag for me is when a syndicator who has no/few exits starts living it up. 

That's less than minimum wage, and that's why THAT business has no value.

If you take that same ambition to real estate, there's no way you'll lose. 

The results of investor’s losing their money may not be any different no matter which “level” above is involved.  

No, you can refinance with anyone and likely the current "lender" is only the loan servicer as most primary residence loans are resold.