We live in San Luis Obispo, at the southern end of the famed Big Sur section of 1 (recently named the most romantic road trip in the US by the Travel Channel). We have driven a 31' gasser without a toad up and down this road a few times.
When are you planning to do this trip? I certainly don't advise it in the rainy winter months. Among other things, the road is prone to long term closures due to weather induced landslides.
Heading N to S, you will be on the ocean side of the road, which can have more spectacular views, but be more white knuckling than the northbound "inside" of the highway, especially for the passenger.
While I don't think it would be a problem in just the 34' coach, adding a towed vehicle would certainly not make it any easier. It is very windy (whine-dy, not winn-dy), lots of hills, and prone to fog this time of year. You will need to use turnouts a lot to let other traffic pass, and once you commit to the road at Carmel or so, the only chicken-out route option to turn inland before Cambria is Nacimiento-Ferguson Road at Kirk Creek campground in the LPNF near Lucia. That route is no better. Otherwise, you'd need to just go all the way, or turn around.
You don't say when you are going to do this. I don't know the state of the highway right now, after these late season rains we have just had. QuickMap
doesn't show any closures or construction at this time.
Also, there is no cell service on most of this stretch of 1, so no ability to use Waze or call for help.
Since you describe yourselves as " We are almost
moderately experienced drivers and prefer to avoid higher risk areas." I would suggest 4 options.
1) Don't do it.
2) Leave the coach in Monterey and drive the toad to check out a lot of it first.
3) Unhitch and have a second driver lead or follow in the toad. Buy a pair of FRS walky talkies to stay in touch (no cell service)
4) If you are committed to the trip and don't want to unhitch, do it another time, northbound.
If you bypass this stretch on 101, you could still drive your combination up to Hearst Castle from Morro Bay, or leave the coach in a campground and drive the toad.
OTOH, big tour buses do it.
Please let us know what your thoughts are.