I have a similar perspective, as I am right on your heels with the same decision, so I'm naturally inspired. 

If you're looking to transact faster than that, then your only option will be private Buyers.Another alternative, other than the ideas mentioned above, might be to sell part of the land into permanent conservation. 

Alternatively, you're a 5 minute drive to the resort.

Alternatively you may decide not to address the capex but be prepared to deal with high frequency maintenance requests with duct tape repairs. 

The other alternative is to raise capital and be more of a fee developer, at least at the start.

I guess I'm one of those "goofy detractors", however I do not recall having levelled anything ad-hominem in nature on this thread (it would be quite out of character).I am not even certain I would call myself a detractor - If someone wants to borrow money to pay-down another debt, that is their business.  

Are there any red flags I should watch out for when dealing with buyers who propose alternative arrangements like this?

To navigate this, consider options like keeping your current home as your primary residence while house hacking a multi-unit property, using the HELOC funds strategically before moving, or exploring alternatives like a bridge loan or cash-out refinance.

The properties are listed on MLS, the owner is a business connection from an alternate venture. 

Compare these with potential financing alternatives, like a DSCR loan or other commercial products.Exit Strategy: What’s your long-term plan—hold for cash flow, refinance, or sell?