If one is simply looking for an auto-pilot shave, I would say Tech.
If you include blade handling in user friendliness, I would choose a Super Speed.
I've got a bunch of vintage Gillettes I haven't gotten around to shaving with yet, but I find my '61 Super Speed to be the most user-friendly of those I've used to date. Effortless, even if it doesn't give me the closest shave in my collection.
Techs aren't as user-friendly for me, because their relative lack of blade feels means I have to pay closer attention to my technique when I'm using them. Incredibly smooth, though.
1964 Gillette Super Speed Hits the sweet spot with TTO ease of use.
For me, it's a dead heat between a post-war Tech and a post-war SuperSpeed.
An Honorable Mention goes to the Yates Winning.
Quite honestly for me, it's between the SuperSpeed and Muhle R89
ASD2 is very good as well, but one can easily lose the effective cutting angle during use.
It would be a toss-up between:
Edwin Jagger DE89
Merkur 42C
King C Gillette
I’d have no hesitation recommending any of these to someone who had never shaved with a DE. The Jagger was my first “proper” DE razor after a Wilkinson Sword Classic (black plastic) and I feel my technique came on leaps and bounds with the Jagger, to the point I felt ready to try a Merkur Futur around 6 months in.
I didn’t use a 42C or King C Gillette until 7-8 years after I first shaved with a DE but I find both to be similarly user friendly to the DE89.
Edwin Jagger DE89, the first razor I bought…