I had 2 upright freezers for many years. One nice thing about newer uprights is some of them have defrost so you don't have to continually thaw out all the ice. My upright that didn't have defrost I'm getting rid of. Ice built up in the door and I often didn't know that the door opened until I started smelling it!
None of the chest freezers I've looked at have defrosters so if there is ice built up you are faced with thawing it out and melting the ice. This may or may not happen very often depending upon the conditions and your freezer.
I just bought a GE chest freezer that is only a few months old on Craigslist for almost 1/2 price. It is designed for garages that have extreme temperature variations. It claims that it only costs around $35/year for electricity.
I always have a couple freezers for capes and meat. I often have several capes, turkeys, fish, etc in my freezer every year. It's nice having enough freezer space that I can freeze entire turkeys until I have time to cape them or place an entire boned deer, elk, or antelope in when the temperatures are super warm and I don't have time to process the meat. I've also placed entire salmon and large trout in the freezer until I have time to skin them. Everyone is a little different but it's sure nice to have lots of space. I'm constantly battling enough room for large items with the uprights I've had and that's the reason I just bought a chest freezer.
Horniac makes a great point, If you have room it may be nice to have both an upright for smaller items and chest freezer for big stuff?