If this were my property, I’d run a detailed rental analysis (from what I’ve read in Forbes) to see if the short term route could outpace traditional leasing.

You don't have to fit into a traditional "avatar" box to bring valuable insight, so don't sell yourself short. :)This is especially true if you rely on furnishedfinder.com as your primary lead source (which you shouldn't, but that's another post) as when you make that connection with a prospective resident, you are selling yourself as a landlord as much as you are the property as a place to live.

It’s my brother and 2 good friends that have some experience. the money lender would be a family member of mine lending out of their self directed IRA so they will be lenient with us.

You will also need about 6 months of reserves deposited in a traditional financial institution rather than a crypto account.The next step is to find the target property and calculate the acquisition costs and costs of construction along with the after-repair value. 

Purchase Terms: Clearly outline the terms for your brother to purchase the property from you, including the timeline and price.To minimize the financial burden on your HELOC, refinance the property into a traditional mortgage as soon as possible.                                                                                           

Reason why is because FDIC Bankers "Do Not" charge points on traditional programs like primary homes, standard investment purchase and refinance, Second home/vacation homes.Lenders, Brokers all charge points to meet their Loan officer compensation plan (commission).

This would allow us to come to the table with less funds out of pocket on the front end when starting construction.Is the best way to complete the transfer of ownership through a traditional sale registered with the county? 

Traditional lending doesn't lend on C5. 

I talked to my lender contact and, as Kerry mentioned above, it's pretty uncommon that a traditional lender would offer a HELOC product on an investment property (non-primary home). 

If you violate any of these rules you could blow up your IRA or 401k and the IRS could force you to distribute all of the assets in the IRA or 401k.