Tim Wieneke , You're both right about both deciding what you want and need, and finding the right balance between not squandering money and not purchasing bulk grains in a shared trailer in a flyover state!

Then, after 4 homes, I realized that if I switched to multifamily I could get to my goals faster because I'm buying in bulk.

If it is still classified as active farmland and your friend has Canadian citizenship then he may be able to use his lifetime capital gains exemption to reduce the amount of capital gains due.   

I bought from a wholesaler once and all he asked for was a reduced wholesale fee and that he be allowed to shadow me during the process from beginning to end.  

So part of my assumption is that repairs will be reduced short term.

My parents are loaning us the bulk of the money for acquisition/rehab and have asked this so reflected on a Deed of Trust.

That has greatly reduced the "stupid trip" calls.       

At 5% down the annual premium goes from 1.35% down to 1.30% not much only 5 basis points but its decent.Only other way to reduce annual MI premium is by using 15 year loans which have a much lower annual premium when you put more money down but it won't be too great for cash flow since the payment is much higher.If you put 10% or more down your MI will fall off when your loan reaches 78% LTV based on the value inside FHA's system called FHA connection (not market value unlike conventional).Most people dont put down 10% anyway maybe 1 out 40 people who uses FHA puts more than the min 3.5% down in my experience.

Whatever "incentive" money you put in the purchase agreement will just go to the bank to reduce the seller's short sale deficit.

You or someone would need to negotiate with the lender to reduce the debt.