So now we're looking at either just me on the loan (using both HELOC and mortgage, with him still paying 50% for my HELOC) OR both of us on the loan (with the down payment still on me).

And if there is a loan guarantee fee on top of the acquisition fee, that is another "upfront" fee that the syndicator can make just for buying a deal.  

Speaking from private/hard money terms, the loan would most likely be considered a delayed purchase if less than ~5 months depending on the lender, and no financing was used on the original purchase.

You could purchase a 4 plex with an FHA loan and live in one unit (house hack). 

Also, it was for an owner occupied duplex, so I was able to leverage better financing terms with an owner occupied loan.

Just barely scrapping by to keep the loan current the best they possibly can.They owe $141k on the first mortgage.

Building positive relationships with tenants can increase their retention and reduce turnover, promoting consistent rental income.Consider FHA loans with lower down payment requirements if you're starting with limited capital.

Conventional loan How did you add value to the deal?

I've closed over 250 DSCR loans since 2021.

IMO the key metric is the DCR. talk to a commercial lender and find out how much they would lend on the property with a convetional loan and then factor in the 25% down and thats your number. i think most banks want 1.2-1.25 in order to lend based on the financials.