Quote from @Cameron Moore: Exactly. 15 years ago, I noticed an increase in owners using insurance to pay for a replacement roof, usually to sweeten the pot during a sale.

The flipper pays 12.5% interest to the lender, and I receive 10% of that.

A good deal for a retail buyer is something they can pay for which has most of the amenities and location they want.

VA loans are the only loans that allow this, and there is no rate penalty for it no longer being your primary home.With that in mind, you could do a cash out refinance today at a higher rate than current market rates which will create profit on the loan, we can take that profit to pay for your closing costs.

We will be paying nearly $50,000/year in property insurance.

My goal is to offer an affordable monthly payment that competes with renting a comparable property and offers a benefit to paying a bit more to "own". 

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

Grow wide first, then deep (pay off)- your little expenses add up fast

I have a followup question - I will realize a lot of capital gain from this home in Idaho, so I think unless I purchase a new primary residence I will have to pay that capital gains tax. 

paying mgt any landscape/snow/utilities?