I went through this same decision process, in fact there is a thread here with some conversation:
https://www.tractorbynet.com/forums...-door-headroom-challenge-lean.html?highlight=
Here is what I ended up doing, work still in progress:
This was the best solution to get the headroom I wanted, however I estimate there was a 40-50% additional time penalty to knit the new roof into the old roof versus just going under the eave for the new roof (with a ledger board). Every step of the process was more complicated and took more time and introduced more "to-do" items that had to get done before the next step.
And of course before I could make forward progress I had to go backwards to tear off the old fascia/soffit, remove soffit blocking under the rafter tails, notch the wood siding to allow the new rafters to reach the header, cut back the gable soffit and fascia to the proper joint angle for the new trim, etc.... I have an asphalt roof, and weaving the new shingles into the old shingles at the transition also took a fair bit of work and preparation, and I put ice/water shield under that area since it is more prone to leaks right there.
So yes, I think it is the "right" approach to tie into the old roof, but be prepared for a lot more BS along the way. I feel like there is no shame in just going under the eave with the new roof attached to a ledger if you are looking for a more productive approach. I would have been done by now if I did that!
You can estimate how much more vertical space you'd gain/lose with each approach and make an informed decision. I gained about 7" of headroom by tying into the roof versus going under the eave, which made a critical difference in door height (slightly more than 7' versus well under 7').
