Hi Myxpyr,
I did it as part of a group of 7 people last July. they were of mixed ability, all managed and enjoyed it.
there are many recent comments on the WHW if you use the search button.
there are many different ways you can go about it.
You can camp all the way.(you will need a camping permit in the Loch Lomond area) this was easily gotten just by phoning a number I got of their web site.
https://www.lochlomond-trossachs.org/contact-us/.
you can carry all your gear.
Or you could use the bag carrier service. This transports the gear to your destination, either camp site or accommodation. Or you can do a combination of both. If I had travelled myself I would have carried. (But having used the facility, would be tempted to do so again) as it was we did a combination of both.
Having only wild camped and carried my own gear in the past on routes picked/designed myself I wasn't sure what to expect, but was very pleasantly surprised, both with the route and the services. The route evolves as you head North, and I feel the best experience would be to do it South to North. It is well sign posted all the way and would be difficult to get lost.
In our experience the piece that you had to most careful on was the path alongside Loch Lomond. People run the whole trail in a day, but that piece must be rough on them.
I had got the impression, listening to "old hands" on the TGO challenge that some looked down on the WHW as a bit Less. But I am glad I did it and thought it a very worthwhile experience.