OK, part of the winter rebuild was the comptip mast and low-profile main blocks. (I'm so old I've never had one) Have the shorter shrouds and the extra chain plate added to the bridle connection.

So, with all this rake, what is the best position for the jib?
Do I attach it on the upper or lower chain plate? Seems like on the lower chain plate we'd be too close (clew to front crossbar/blocks).
Orrrr, since all Boats/setups are slightly different what's a good starting point?

That's a tough one - depends on a lot of things:

What's your jib sheet stack-up?
How old's the jib (post-2000 have a more "rake-friendly" cut.

Start with the jib in the middle of the lower adjuster. Tension the halyard 'til it's "firm" (not necessary to get it super tight.

Downhaul the main to just get the wrinkles out.

With the boat on the beach, sheet the main in until the leech is parallel with the mast (not hooked - stand behind the boat and watch the top of the sail as you sheet in - you'll see when it hooks). You should end up with about 6"-8" between the blocks - not two blocked (When you're sailing, the force of the wind will blow the leech open when you're two-blocked.)

Now sheet in the jib. If it goes two blocked without much effort, you need to move it up in the forestay adjuster. Ideally, it should get firm with a couple of inches to go before it's two-blocked.

Once you get it to a point where everything is good, remember the hole in the adjuster and mark the halyard at the black band. That way, you have reference points to set it up the next time.

All makes sense, thank you sir. We'll be doing this Saturday morning before the first shape (darn winter projects take longer than expected).
We're pre-2000 sail and jib car w/block, we'll start towards the top of the lower adjuster.