I guess the bigger question is, does the income on Property 2 look enticing enough to keep barely breaking even in hopes of the day we can refinance it favorably?

I think that you need a better inspector and inspection check list... that seems to be where the break down is.

If I break even on mortgage payments and don't cashflow I count it as a win.

Lets say its 1k a month on a quad, your partner would be losing out on 25% of income, while you would actually be getting the full 100% plus some on the break from living expense. 

It's not unusual to see 3/1 and 4/1 Section 8 properties but that single bathroom would not do well as an MTR.Overall, I'd say location and the shape of the property is going to be your key driver and the factors that will make or break you in the MTR space so very carefully evaluate both before you make your decision. 

In the end they hope to be positive from losing some, breaking even, and then making money over so many properties (rehab portfolio averaging).  

Overall the house hacking achieves effectively living for break even or less than rent and getting you into a market you normally couldn't afford the downpayment on.

He’s breaking the lease after only 4 months after getting transferred.

It looks to be break even currently, but every year after when the price of electric goes up is where the savings would be, assuming the usage doesn't change much.

My current primary ( scenario 1) Keep the primary for the life of the loan ( current rate is 4.5 so i dont see my self refinancing anytime soon)current home value 1,150,000Loan amount 935,000appreciation estimate 5% per year after a 28 year hold and the house is paid off I would have a house worth 4,312,000$my current mortgage is 6125$ ( piti) included My second option( scenario 2) Sell the house, walk away with $150 ,000 ish in hand and put that into a low cost index fund Rent a house elsewhere for about 3000$ ish and take the extra 3000$ im saving everymonths from not having to pay my mortgage and puting that money in the index fund as well I ran the numbers on both of these scenarios and doing what I mentioned above would break even at about 28 years meaning my stock account would be worth 4.3 million just like my house would , but the only is that holding a house for 28 year would mean 28 years of property taxes, loan interest ,home insurance and repairs etc whick I calculated to be about 1,200,000$ at minimum which raised my eyebrows to say the least Also i understand that each of these options ( stock market vs real estate ) will have there tax consequences ( long term capital gains) so any thoughts on that would be appreciated as well.