Installing window channel weatherstripping

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Getting ready to order my weather stripping, which also may mean I'll be getting my interior painted sooner than I thought since I don't want to put the stripping on just to take it off soon to paint (and possibly ruin it in the process). The painter is a friend of ours so will work out a good deal to get it done.

Trying to plan ahead so I can be prepared for problems and have a better idea of how to do it.
I was noticing that the window channel stripping goes almost all the way down into the door. Is this a pita to replace? What worked best for those of you that have done it?

I'm going to be doing the doors and both door windows (vents too).

Any suggestions or words of wisdom to help me get through this?

Also a quick update on the status of everything else I've been talking about recently....

1.) Upholstered door panels and dash is installed

2.) Painted bezel (light grey) to match upholstery (dark grey and light grey) turned out better than I thought it would Might do brushed alum bezel eventually, but this works good for now.

3.) Bucket seats have a new frame welded to them and are sitting in my living room waiting for brackets to mount into truck. (To be done when center console arrives...unless I get impatient)

4.) Fold down center console seat is ordered and should arrive in approx 5 weeks

Ummm...I think that's about it for now. Sorry guys, no pics till the seats are in!!