If you've been living in the property for 5 years, you won't have to pay capital gains taxes as well. 

I keep telling him that we’ll need to jump on something once the flip is done otherwise we’ll be paying more in taxes. 

If you are house hacking to have someone else pay your mortgage what would be the point of a separate account if you are just going to switch it over to your checking or directly into your mortgage. 

Have you been aggressively paying down your mortgage while you are in there to earn even more equity over the longer term? 

There were on sale and I didn't have to pay for sales tax in Portland OR.

Maybe you could hook up with one of these battered women groups, and turn the place into a shelter for battered women, Where the charity would pay for all of the rooms and just use them as needed. 

I am struggling to decide whether to get into this home or narrow down to a property that is $310k and can pay for the mortgage right out of the gate?

I no longer qualified for traditional financing because I already own many rental properties and my DTI was high for the bank, so I purchased these in a business entity with a trusted private investor and was able to refi the 1st property/sell the 2nd property to pay back my investor and ultimately keep the better property for zero money down.

I may even sweeten the pot and offer to pay them a few thousand to help them with moving costs.

That will help you to pay your mortgage.