When I was first starting, I saw a few posts that recommend that I go to the final tire size first, and then worry about the rest of it. So I went straight to 35 inch tires, as that was the largest I could reasonably do.
I've had a few hiccups along the way, and am far from my goal. But I still agree with the logic.
For example, I want to airbag my Jeep to adjust to changing load conditions. (I haven't decided whether to go with a simple system like the Air Lift 1000 bags or a full on air suspension like the Airock.) If I had started with that on a stock Jeep, every time I changed the lift height or tires or body lift or shocks, I would have to readjust the bumpstops, shock length, air bag size, etc. But being at the final tire size makes it all permanent. No temporary measures. No swapping airbags. And all of the effort spent tuning it goes into the final product.
I am far from done. I'm probably currently much more capable than a stock Rubicon. But I do not regret going to 35s, as everything I do goes to improve it.
Driving 70 mph on 35s for the first time was a 2 hand affair. Now that I have it somewhat tuned, driving 80 is a one handed affair. Eventually, I hope to get to the point where 80 mph becomes a one finger affair, and I can comfortably push it to 90 to pass if necessary.
So no, I do not regret going to 35s. The key is to avoid the "gradual" aspect. Bite the bullet and start where you want to be. Then make it work.