I would suspect there are two issues that are preventing you from achieving ideal shaves with the Timeless. Firstly, I suspect your choice of the long handle is at play, it's certainly not a handle for everyone, I selected mine based on previous experience and having big hands, I struggle with shorter handles (Fatboy, Slim, Merkur Progress Standard). I'm not sure whether you chose your barber pole handle based on how mine looks or on the functional preference, if it's the former if I were you I would look at obtaining a handle much more suitable to your physicality and I think this will go a long way in correcting the deficiencies you are experiencing from the razor in your shaves.
The second issue I would suspect is transitioning from the Rockwell that weighs 113 grams complete to the Timeless that (with Barberpoll handle and Scalloped Cap) comes in at 144 grams - a significant weight difference.
The Timeless requires a highly proficient technique from a technical standpoint, I teeter on the edge of using negative pressure when shaving with it as the weight of the razor alone is more than sufficient to deliver incredibly close shaves. You may be subconsciously applying the same pressure you would with the Rockwell and this is going to cause you issues with a Timeless, even using the milder 0.68mm plate.
When I shave with my timeless it's purely the weight of the razor alone shearing the facial growth, the weighting of the Timeless is perfect and when held at the correct balance point you can feel the balance of the razor in your hand and it glides down the face with an audible resonance - no skipping, no sliding just a very precise, tight shearing of the bristles. Obviously your choice of blade selection is important here but all things being equal if you are using a sharp, new blade flawless shaves are easily achievable if the balance, hold and handle length are correct.
