To plastic or not to plastic?

Ok, where to start?

I have a 990S that I really enjoy. Like really, really, love the bike. It's great.
But... There is always a but...

I'm thinking that I want to ride more technical stuff than what I'd be happy doing on the 990.
It's probably just too big and heavy to do stuff like the old postal route as an example and some of the lekker places I've taken my Land Cruiser.

Now, I don't want to have to trailer a bike from home to the start of the fun stuff, so road legal is a must.
Comfortable enough to do say 200km from home to get to where I'm going and then spend a weekend away doing some fun stuff before heading home.
Yes, its probably a bit much to ask of 1 bike.

So what to do?
A 690 with some Omega kit could probably do it just nicely and is a nice compromise between say a 500/525 KTM or a WRF450 and the 990, but then I would have to sell the 990.
Buying a decent 500/450 could be an option and can be done fairly cheaply.
Perhaps I should start with some Enduro type riding locally 1st? Where and with what bike?

What other considerations/options are there?
This is a big can of worms I'm opening here!