Kudos to your band for your setup! It sounds pretty liberating! Do you have a tech running everything for you, or does one of the band members do it? I'd stress too much over the system crashing. lol.
I am essentially the designer, engineer, and tech for the band's rack lol. Our system actually goes a good bit further but I didn't get into all of the details since this was specifically about midi and dmx lighting.
I don't worry too much about the system crashing as we use it for every rehearsal, and any time a problem comes up, that's my task for the week. My career is software and hardware testing, so in my non rehearsal time I'm pretty good at diagnosing what happened and then implementing a solution. At this point almost everything is seamless. With that said, there are times where we will not play with the click tracks or stop them in the middle of the song so that we practice if the system has a meltdown. I like the automation this tech has given us, but I don't want to lose the ability to finish the show if we lose the click tracks.
In terms of running the show, I've actually routed a Voodoo Labs Ground Control Pro up to Reaper via the Axe FX 3's midi passthrough. The GCP has been programmed to allow me to dynamically select songs at will and it will select the song in Reaper and then I have a Play/Pause button assigned as well. This allows my group the flexibility to change songs on the fly if I want. Most other click track solutions require you to go in order without the ability to select at will. We've also programmed some pauses in the middle of songs so that we can loop measures on our own or just do a dramatic pause etc, and then I can click the Play/Pause button again to start.
If you're looking to do the biggest show setup upgrade outside of the dmx lighting stuff, and if you run drums with microphones, I would recommend getting a microphone snake that has 8 xlrs to a db25 connector along with a drum rack. I've designed my drum system with a drum rack where you take the drum rack apart into 3 pieces, and the entire kit moves. The kick is mounted to the middle rack system. Once you get to a show, the hi-hat rack arm mounts to the main drum rack and 2 people pick up the kick, top toms, cymbals, and hi-hat and get it on stage. The floor toms are permanently mounted to another rack arm and 1 - 2 people can get that on stage. In a single group move, the entire drum kit goes on. Almost all of the drum mics are permanently mounted and connected, even during travel. You just need to connect 2 floor toms, and a snare. 2 overheads are permanently mounted and mic'd. With the db25 snake, there's a rack mounted db25 to 8 xlr port converter that's pre-wired to our x32.
Essentially the flow then becomes: Drum kit on stage -> connect 3 mics to the toms and snare -> connect 1 db25 snake to the back of the rack -> power on the rack. Drums are ready to perform and once the Axe FX units boot up the guitars are ready to perform. I designed our rack to be able to get on stage and going very quickly. We can get the whole thing on stage, connected, and be ready to perform within about 5 minutes, less if you have 1 or 2 friends helping to get all of the vocal mics on stage.