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? 

Good luck

Good luck!

I don't see much information regarding this company. https://s8academy.com/section8Or have you had any good experience with any other programs?

My name is Zapa, and I am born and raised in good ole Kentucky!

Banks with 2-10 branches are often good.   

If you're willing and able, I do recommend the "house hacking" strategy which is just a fancy name for buying a rental property and living in one of the units, because you'll get very favorable financing - an owner-occupied fixed-rate 30-year mortgage.I'd also say, analyze that property as if you won't live there and it's a pure rental, and make sure the property is still cash flow positive if there's a tenant in your unit because then you'll know if it's actually a good investment.And when you analyze it, include payment of a property manager in your #s because if you don't, and doing so would make it go cash flow negative, then you've just bought yourself a job because you literally can't step away from managing it without losing money.

Sounds like you have a good plan moving forward for your investments and great markets selected for BRRRRs. 

If the answers match, you’re probably in good hands.

Good things take time.