For example, on a conventional loan, you have to wait 12 months from when you purchased the property to use the NEW value to walk away with cash in hand. 

As I would need a work history for 2 years to get a conventional loan.Thanks for your help!

They can also be great for situations where you are looking to secure a property with more conventional financing, but don't have enough time to close with the original financing.

While this would improve the cashflow and cap rate for resale, I'm wondering if it would shrink my market of buyers, since they could no longer use conventional financing as it would no longer conform to a 2-4 unit building.

You can go FHA or conventional on your 1st home but, if you go conventional on your first, you'll more than likely have to go conventional on the next one.

Conventional mortgages can't happen at that pace without a significant income (or your rental income is significantly higher than the debt repayments).

I'd suggest these for Cash flow / appreciation: Christian Park (C class)Bean Creek (C class) Garfield Park (B class) Irvington (B class) Emerson Heights / Bosart Brown / Little Flower (C+ class) Near Eastside (not so much Tuxedo Park - C+ class) Parts of the Near Westside near Hawthorne (C to C- class) Riverside (depends here...

9) adding multiple ADUs or adding an ADU to a quad looses F/F conventional financing.

If so, you could do an FHA loan with 3.5% down or conventional with 5% and live in it for at least a year.

Since it is conventional financing, then your friend/wholesaler may not even qualify without predictable income for 2+ years.