The digital programmable remotes/receivers usually allow for 3+ models to be programmed into it. So if you have 4 vehicles, you use one transmitter and just switch model numbers (and possibly crystals if you don't use 2.4G) and go.
Personally, I wouldn't get anything less than a 4 model memory 2.4Ghz setup. Even if you have just two trucks, it means you can setup the remote for a family member to drive that has limited throttle without futzing with it. Just switch the model and hand them the remote. Then when you drive, switch it back. This requires you to setup the remote twice for each vehicle, but once it's set, your done. Then if you buy another down the line, you can just get another receiver and use one of the models on the remote to switch to and use.
I run 4 trucks off my one remote. I have an older spektrum DX3.0 which has a 4 model memory. That's pretty much keeping me from buying more trucks... lol
So, full adjustability of the remote, multiple models, better technology to give less interference and longer range. Those are usually the reasons why people upgrade to a better setup.