TS20xx and TSW are different things. They probably share some code (similar to FSX and the now abandoned FSW), but while some external addons may theoretically be compatible, it usually won't work. DLC on Steam is strictly tied to the product, so you won't be able to install DLC for TS20xx in TSW. TS2018 vs. TS2019 might be like FSX/P3Dv3 vs P3Dv4, so some addons will work out of the box, some will need an update (and otherwise won't work with a 64bit TS20xx), some might need a new purchase (because many developers need money to be able to invest time into an old product, and porting something to 64bit needs time).
Until now upgrades from e.g. TS2014 to TS2015 to ... to TS2018 happened automatically on Steam, so if you want to stay at an older version, you will have to disable automatic updates.
But I assume that if TS2019 causes too many incompatibilities, there will be a way to either install both at the same time (like e.g. Wasteland 2 and Wasteland 2 Director's Cut, where owners of the old game automatically received the new one on Steam in addition to the old) or switch between 32 or 64bit installations in the context menu of the game (either via Properties->Betas or two different launch options).
If you are happy with TS20xx and don't miss anything that is included in TSW (or available as a DLC only for TSW), then I'd recommend staying with your current sim
If you intend to buy large amounts of DLC, be aware that: - you can't use it on the other sim, so switching will be harder - the DLC may not be available in a 64bit version of TS20xx at first (or at all, or needs a new purchase)
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