Where the argument hinges is on the lot separation. 

I second what Jonathan Greene is saying here—turnkey is probably best bet given your constraints.

15 acres for a lot sounds huge to me and I'll bet you could be missing out on some extra $ by not getting more lots.

It has been mentioned above but your best bet is to separate the SFR and the 8 unit into two separate transactions.

Hey @Jon Pflueger - your best bet will be to retain an architect, they typically have a good understanding of what's feasible and not in a specific zoning/area + will know how to handle variance permissions and etc. 

I’m also not a fan of buying a property that loses money every month, while hoping for appreciation and betting that interest rates will fall.

It's hard to say for sure without knowing your market numbers, but I would bet you if you looked at a 10 year projection, you will probably have a better ROI with the equity in 2 houses as opposed to the equity and cash flow with one. 

While the allure of short-term rental tax savings is undeniable, success hinges on attention to detail.

thanks Your best bet is to partner with a GC or find a GC that a friend of yours trusts.

i think your best bet is to try to build a network within the investing world so you're positioned as a hub, someone who knows a lot of people, and see a lot of transactions.