Upgrading High Sierra to Catalina on 2016 MBP using local webserver

In the past colleagues (and I) believed it was often a bad idea to install newer OSs on older Macs. I get the feeling that has changed, and that putting Catalina on my 2016 MacBook Pro shouldn't be a problem. What I'm wondering about is whether my local webserver will survive the upgrade. I have Apache/MySQL/PHP set up in the same approximate manner as we were told to do this years ago - sites running in /Library/WebServer/Documents, custom hosts and httpd-vhosts.conf files in /private/etc and so on. In past os upgrades and moves to new machines it's been necessary to re-set-up all that, which isn't a huge problem but also not a lot of fun. In the past it helped that I was migrating to a new machine, so I had access to my whole old setup and could do things like export MySQL databases from the old and import into the new. This time I'm thinking about upgrading my existing machine so I won't have easy access to a backup while I'm doing this. I hate the thought of buying a new machine just so I can upgrade the OS. On the other hand this is my work machine and it's 4 years old (and has a dead speaker) so perhaps it's time to bite the bullet. Any of you experienced migrators have an opinion about which way I should go?