@Brittney Yang first red flag is it doesn’t sound like he’s that interested in long term holds but the primary reason for partnership is expertise in renovation and secondary reason is balance sheet and income to help get financing.Regarding reason one, I would offer to compensate him for his time in assisting you and have a very clear scope of what that responsibility is.  

Maybe it’s just gut feel, but for some reason It FEELS like these two scenarios will provide excellent opportunities moving forward, while fishing for notes to purchase at significant discounts to current principal enough to yield sufficient returns doesn’t seem as promising.  

It's eating away every bit of cash flow from the property and then some.Both units currently have baseboard heating - which I've heard can be on the more expensive side of heating options - but I'm not sure if this amount is realistic for the area, or if there is a better heating option that I should look into for a reasonable cost.

I dont see any reason why the market would go up with the number of new buildings they are putting into the city as well as factors mentioned above.

Having an experienced GC build their first deal or two of their own is, for reasons that sometimes don't make sense, get push-back.

I didn't negotiate a ton on price as the deal seemed pretty reasonable.

Then can decide for whatever reason not to fund the loan and keep that engagement fee.

Because Zelle requires more data entry I would explain with the new lease there will be a small and reasonable processing fee if the tenant kept with zelle but they can still use it.

They care about what they estimate it would cost to rebuild the home.All else being equal, yes, older homes are more expensive to insure than newer homes for a variety of reasons. 

Jeff and John are extremely reasonable and may give you a handful more great ideas based of what your end goal is.