There are other FHA requirements concerning which you should contact your local lender, but determining whether or not a triplex or fourplex meets the self-sufficiency rule is a good place to start as this rule will immediately eliminate many properties from your search.Good luck and reach out to me with any questions!

One of the things we have learned to do is eliminate vacancy as much as possible.

Would a FHA Loan eliminate the 20-30% down payment?

There are other FHA requirements, of course, concerning which you should contact your local lender, but determining whether or not a triplex or fourplex meets the self-sufficiency rule is a good place to start as this rule will immediately eliminate many properties from your search, especially in expensive markets like ours.In terms of your questions, I'd say $1k/month is a bit ambitious if you're living in one of the units.  

If the property is cash flowing positive, I'm not s big fan of eliminating to mortgage on it all at once either.  

This would eliminate PMI from FHA loan, but interest rate will increase significantly.CURRENT LOANSingle Family HomeValue: $130,000Principal amount: $73,300Term: 30 Year FixedCurrent Rate: 3.75%FHA Monthly PMI: $83Mortgage: $779/month (all costs included)Rental Income: $1,175REFINANCE LOANLoan amount: $97,500 (75% of equity)Closing costs/fees: $3,900Cash back at closing: $20,300Interest Rate: 4.875Conventional FinancingMortgage: $790 (all costs included)Rental Income: $1,175Regards,Nate Barbee

Otherwise the bank likely knows nothing about this and no private auction will eliminate them.

I am on an HOA Board, and I believe  we could push for some sort of change - either elimination of the transfer fee, or a cap/limit to the fee.  

Speaking from experience, it is precisely as John says, making the work far more manageable for the contractor if a particular phase can be focused on, and with the ongoing cashflow by way of draws it helps to eliminate any potential issues with the guy "running out of money". 

Lastly we are looking to combining both parcels which shouldn't be too much of a problem and would eliminate both of these problems.