Their goal is to move in for a time then sell and roll all the appreciation into a larger property to live in. 

@Jeff ShumwayThat's sounds like a down payment assistance program, where you roll over some closing costs into the loan at the price of a higher interest rate.

I usually roll with the mindset of do the renovations that would allow me to feel good about renting to another human being.

It would be great for a few months, to accelerate savings some, and get the ball rolling on some real estate investments, but definitely not a long term option.

If you a fixated on "your guy"..... you fully trust their ability, honesty and price..... and don't want to risk using someone else, then explain that to the tenant....be honest and up front about it with them....... and provide several portable units.When it comes to contractors, I 100% understand not rolling the dice on an unknown...... be honest with the tenant about why you are doing what you are doing and provide a reasonable temp fix with the portables......

Who I hope to keep on if I can keep the ball rolling as a true company along the way She loves her job but causes deep stresses between her lack of family time and feeling she’s missing out.

Sell one property and use the proceeds to roll into buying two more rental proeprties.

The stock market has a long history of growth and until you have some personal experience in real estate investing you should be cautious with your retirement accounts.I would suggest rolling the 401(k) funds into an IRA and doing annual Roth conversions each year to fill up the lower tax brackets. 5 years after you convert a portion of your IRA to a Roth it is counted as the “basis” and can be taken out of the account without any taxes or penalties.

I would want to see the rent roll to see what is actually coming in and from what units and the trailing 12 months expenses to track what is going out.Once you have this info you can compare to the market.

Are you covering the utility bills and rolling them into the rent?