So here are my new assumptions: *Purchase price $45,000*Upgrades/Rehab Estimate $10,000 (could be a ton less but I've heard you should over shoot)*Total Cost = $55,000Mortgage Estimate (15yr mortgage, 4%): $380.00/mo Property Taxes: $25/mo (per the city records lookup)Home Owners Assoc: $150/moAdditional Cushion: $150/moTotal Costs: $705/moRental Potential for 1bd/1ba in the area = $850/moPotential Monthly Cashflow: $145/mo Those of you that flip houses, it sounds like this would be a horrible flip, mostly because the ceiling on the sales price would be in the $60's and that leaves me only $5K which will be eaten up in realtor and closing costs.Am I thinking along the right path here?

My plan was to buy my first property while I'm living rent free so I've got a cushion in case something goes wrong and then once I get a handle on landlording and save up enough cash for a second purchase, house-hack through an FHA or low % down conventional on a duplex in my area. 

I wouldn't plan to move in until the lease is up.I am capable of covering both rent (within reason) for a new apartment and my mortgage/hoa but it leaves no cushion.  

In five years we should have a good chunk of $$ in the bank and, if, as I hope, she gets scholarships etc to pay for her undergrad those properties can continue to give her an income cushion or can be cashed out to pay for grad school.  

Partnering may allow you to cushion that blow, but it also could risk giving that idea to that person to test out without you.

What is is a good savings cushion as a percent of the initial investment?

We don’t need another crash like in ‘08 with too many people buying houses they can’t afford. 20% down will give you the cushion you may need later.

.,   As you've gotten multiple offers and all are in the same range and apparently not accepting your counteroffer, it appears those looking at it want more cushion than you feel is necessary. 

Do you have the cushion in your cash flow to cover an extended period of vacancy in several of your units?

Although a higher down payment doesn't mean a buyer won't default, it would offer you a larger cushion if they do.