Our occupancy during our off season is near zero.

The lender does charge the flipper 4 points upfront, and the note represents 55% of the property’s ARV, so I’m not too worried about needing to foreclose if it comes to that.The lender uses his own capital for initial funding and then sells off the notes after that.

Some days I feel confident and then other days I'm worried about a ton of things like (what if I get ripped off).

It would be a good idea to assess your tolerance to risk and then plan something like that, but using a heloc is going to be around 9-11% in this market so to pay something off with lower interest rate to borrow more might not make much sense.

Property values continue to grow in value, and you can actually live off the rental income.I think it's best to hav all properties paid off by retirement age, since that's when you are going to rely on cash flow for your living expenses.

I invested to test out the process in the short term, as it was supposed to "mature" and be paid off in March 2024, and here we are in December. 

If you can make me believe your vision makes $, and that your the guy to pull it off, I'm handing you $ in proportion to what my reward can be for it, and how certain I believe you can deliver on it.  

Cold calling is a great idea to get started, but maybe try connecting with local real estate groups or online forums too—they can sometimes have off-market deals.

My belief is you are off by at least 5x. 

With that said, here is an opinion: You cannot write off anything you use as a personal residence.