Indeed- sounds like Mavericks was not kind to you. That stuff happens, as we have all suffered. I haven't had any significant problems yet on my MBP. A little flakiness with the trackpad. But yesterday I gave it power workout and it seems OK. Nothing else to report. That disk is running a system that started in Leopard and has gone through several migrations and upgrades.
Until upgrading becomes compelling, my Mac Mini is still running ML. I did upgrade and then restored back, but Mavericks seemed to be OK. One thing is that if you upgrade a Mac Mini, your monitor calibration will be thrown way off and you'll be greeted by a ghostly, washed out screen. More than you'd think, calibrating third party monitor's to Macs can be a real pain.
i don't know if you run them, and many people poo poo on them as unnecessary, but there are ten or so maintenance scripts out there that you can find online or on these boards, and I swear by them (but maybe it's just a placebo). I like to run them every month or so (or when the system seems flakey) from Terminal. I've hear that Repair Prebindings is no longer necessary for example, but I still do it. Can't hurt anyway.
I'd be curious to know which programs were incompatible for you- I only had two, and I'm really happy neither was PS or AI. Also, you probably know there are uninstallers you can download that will delete the related plist folders, etc., along with the app folder. If I lost apps that I paid substantial money for, I'd be reluctant to upgrade. I did lose 13 bucks on one...
I've been fortunate- I haven't had any major problems since OS X came out, though I've had headaches and many spinning beachballs of course. The worst thing that happened to me was the 2009 (?) iMac with the bad power board. Yep, the machine died just a week after warranty. Right after I got divorced too come to think of it. Maybe it was a bad omen.