Rush slowly. There is rarely a compelling reason to rush to a new major OS Upgrade as soon as it is released. This is still true of MacOS Catalina (MacOS 10.15.x) which Apple has just released.
Catalina is the first version of MacOS to STOP support for 32-bit applications. This means many of your old Apps or those who have older ‘plug-ins’ or utilities may not work. Lack of support for 32-bit apps is perhaps another good reason to delay a Catalina update.
Notable among early issues reported by some users are relatively minor bugs with the latest Adobe versions of Photoshop and Lightroom.
Team Digital always recommend waiting to confirm that all applications, especially those critical to your workflow, are compatible with a new OS before you upgrade. This often means waiting as long as six to nine months after release.
The opposite is true of minor ‘security’ updates which as a matter of practice should be installed on your system as soon as they are released.
Perhaps your wisest course of action might be to leave your trip to ‘Catalina’ until at least 2020.