Apologies if this has been discussed; but I was thinking about the following: As we all know, TSW4 content is not compatible with TSW3 - following the same logic, what if I build a route with the new editor, and TSW5 comes out a year later: - Do I need to update the whole route to make it complatible with TSW5? This is especially tricky if it is a payware route, as the developer needs to update it to make it compatible with the new version. Also, this could create a lot of abandonware if the developer decides not to provide further support. - Will a route created with TSW5's editor be compatible with TSW4? If not, then you will always have to buy the latest version, which is completely different than TSC - this could cause a lot of issues further down the line.
I think it wouldn't be too much of a problem to upgrade a route to be "TSW compatible content" as older routes released for previous versions are described as. It would be if the engine version changes, which I think it something DTG will rarely do now given previous experience. If the route is payware, it must be distributed through Dovetail Games under the licencing agreement with Epic Games (the makers of the Unreal Engine), therefore I would expect this would be planned in as you would have to be an active partner with DTG to be able to make any money at all. Doing this outside of DTG would be a breach of terms with Epic Games and is explicitly stated as not permitted. Your last question has already been answered by yourself at the top of your post because the TSW4 routes are not compatible with TSW3. This would most likely be the case for future releases.
The problem is that for any sort of modding community to work, being "not too much of a problem" isn't good enough - it has to not be a problem at all.