To update Wine you simply need to go to the graphical package manager of your distro, also called "Software Store" and update it.

And it would be interesting more context to help you about your configuration and machine, because I doubt very much that an upgrade of Wine will make a program run or not, it depends on much more things, as precisely the dependencies of the program itself.

Bottles makes it really easy to install all dependencies you need and experiment with different versions. https://usebottles.com/

Have you checked for compatibility with the programs that are crashing? Before you go through the effort of installing everything, it's worth checking if anyone else got it to work: https://appdb.winehq.org/

As for upgrading, that would depend on the distro you're running. What do you use?

Is there any dependencies the program requires? Usually missing dependencies is the cause for some wine crashes.

I would highly recommend using a Wine manager program such as PlayOnLinux. You can have each program in its own virtual drive and can use different wine versions and tweaks for each program. It'll manage the wine versions in the app so you don't have to install it systemwide.

Also check out https://appdb.winehq.org and https://protondb.com for compatibility, tweaks, etc. for each program.

Install Windows. Running Windows apps on Linux doesn't promote native development of apps for Linux.