As someone with both the handy and the original Fleshlight Launch, here are what I personally think are the important factors to consider:
1) Case & Sleeve Compatibility
In my experience, it's much better to have a hard case. There are several problems with soft sleeve only (e.g. the default handy setup):
It comes loose easily
You can't grip it too tightly without it being unenjoyable for the penis. But this means that it can come loose easily, especially if you don't maintain an erection the whole time. This is particularly an issue when going from video to video, some of which may not have scripts. With a hard case, you can tighten it as hard as you can without it affecting your experience.
Insertion is easier with a hard case
That being said, it is possible to use a hard case with the handy. Ever since I started using a Fleshlight quickshot, my experience has been much better.
2) Script loading times - Bluetooth vs server sync
Do you want your scripts to load instantaneously (bluetooth) or are you happy to wait 15 secs in between every video (server)? The latter could potentially make your penis go soft and if you have a soft sleeve only setup, this could potentially mean the sleeve loosening.
3) Portability vs power
Battery operated toys (e.g. Fleshlight Launch) need to be regularly recharged but can easily be taken to the bathroom, the bedroom, the sofa or any other place you'd like to use it.
Toys that need to be connected to an outlet (e.g. the handy) have a more powerful motor but can only be used close to a power source. It's also a lot less convenient moving it around due to the power adaptor and the needing to replug it every time.
4) Noise levels
Do you need to be discreet when you're using it? Some are noisier than others and your wife/kids/housemates may know exactly what you're up to.