hold for 5 years and sell or hold forever?

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

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

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.

You are VERY easily able to open accounts remotely by just uploading your EIN doc and then once your biz account is open you can open additional accounts for things like holding your security deposits, reserves, etc.

Also I feel buy and holds are harder to structure partnerships as its not that much money when split in between two people.

Investment Info:Townhouse buy & hold investment.

If we are losing money every year, but do plan on holding on to it long term, with our goal being appreciation of the market and someone else paying a good chunk of our mortgage, is this worth doing on any level? 

With interest rates holding steady (so far) and US Treasury yields hovering in the 4-5% range, many investors are weighing the pros and cons of staying in bonds versus seeking opportunities in real estate.