This also only works for cash buyers willing to buy and hold. 

You'll have to factor that into the holding costs as well. 

hold for 5 years and sell or hold forever?

I'm an active duty military member and our family has been moving around the country for the past 20 years so we're excited to begin buying some places we can hold onto.

Is it smarter to hold onto the house and keep renting it out, or sell now and roll the equity into the new home?

Roll them all up and the averages are:purchase $154krenovate $47Ksell $232kThese are gross numbers, not including closing costs, borrowing costs, holding costs, licensing and permit costs, G&A, overhead, commissions, forward rate buy-downs, and lease-up fees, to name a few of the many expenses incurred. 

We have been house hacking in Boise, property to property for the last 5 years - and they all were not break even or positive after we left, and we have paid monthly out of pocket to hold properties. 

I think your biggest issue with any "work-arounds" is going to be your legal liability and holding the proper insurance in case something goes wrong, which I'm going to assume you'd need to be properly licensed in order to be properly covered by insurance.

Supposedly they have had a deal for me in Florida that has had title issues that has been holding it up from closing.

Being a real estate forum everyone will tell you to hold forever and keep renting it out.