So more tax's = higher prices as that cost is passed-through to YOU the consumer, and higher price = more profit in that % profit margin. 

So, I accepted modest appreciation (doesn't really look that modest since about 2020, honestly), and enjoyed a steady income. 

What has happened is the consumer expectations has changed and now owners who are use to a different consumer must change or deal with complaints and/or low occupancy.

This negative initial position can consume years of the cash flow.  

Do you think parterning with a guy whose content I’ve consumed on instagram and youtube is to unreliable and “scammy”?

Without an exact numbers breakdown of each option (which should obviously be my next step), I think my ideal situation would be to sell the SF and roll the equity into this, leaving me with a modest holding cost that I can absorb with my stable W2, and keeping the HELOC for any larger ticket items I need during rehab.

If the modest rate improvement you believe you can obtain having the real estate titled to your name makes the property financially work, its probably not a property you should buy.

Okay then you're in a really great place, if you had 250k of consumer debt that would change the focus a little!

Considering the amount of equity between the two properties, we are looking for a relatively modest $250K loan on either of the properties... whichever would be less expensive.

There is a lot of mistrust in lending from both the private money and consumer purpose side.