So if your goal is to create some passive income from REI, I would say do the work to get over the paralysis and execute your original plan.

The starting point is to find and hire a qualified intermediary to guide you through the process.

We had friends move close to Frogtown in the Como neighborhoods, not sure which but that could also be a possibility.

Typically with assumable mortgages, the actual borrowing entity can only have one purpose, which is to own and operate the collateral and no other assets.

It seems like the general consensus is to utilize a HELOC over a HEL to fund my first deal and then follow the BRRR strategy to keep the HELOC open for future deals. 

If you are holding in cash, it's not as important, but if financing or refinancing is to be used in your strategies... you better understand how the bank looks at things.

If it is to help you fund a deal, that can be a very risky strategy.If it is to make it easier to track your expenses, almost any credit card would work but I would recommend one that doesn't charge annual fees. 

It seems the common concencus is to keep the property for rental income . 

Our plan is to buy a small multifamily with owner-occupant financing then buy another property to live in after living there for one year.

Seems like the cash flow is close to 0 which is not bad if your goal is to hold until it's free and clear. from the rent/purchase-price ratio it seems like a decent rental and cash flows positive if you do 30 yr which is something to think about.