[LH Lead-Foot]

I like the look of the drip rail trim and I also agree it is going to be a pain. Working at a dealer on new vehicles, some repairs required removal and re-installation of exterior trim. I would use masking tape to keep from scraping new paint. While tabs or plastic retainers is more common, the old school drip rail trim is friction fit which raises certain issues.
#1 Will it scrape some paint of the top or bottom edge when rolling it on? Both.
#2 Drip rails are not perfect from the factory so more attention maybe needed to make all things equal which takes time & effort, before painting.
#3 Get a buddy that does not loose their temper easy, otherwise it will get bent.
#4 I was told years ago, that plastic wrap was taped in place, then the molding was rolled onto the rail. Then the plastic was trimmed away after the install.
Never saw it done but sounds good.

I worked with a guy who started a GM with a broom the day after he graduated from high school and still is there. His dad worked at a truck plant for 20+ years, before they moved it out of town. His dad is gone, but Bobby G. can recall many things he saw and heard how things went together.
I never work at Goodyear, but 3 family member did. We went to open house events to see tires being made and the equipment used. Amazing, but if most saw how, they would not trust tires again!