I had a problem like that. The caulking does move with the flexing from the roof etc and it WILL leak. I ended up using gorilla tape last year to seal the PS until I got home from an extended trip. It was a mess. I found several spots were the fasteners were broken off . I found those when I pulled off the tape and the fastener heads came with it along with several strips of poorly adhered paint. I ended up repairing it myself and repainted the area. There was someone on the “ other “ Tiffin site that had the same problem on the DS over the seat area. That was a couple of years ago and Tiffin paid for it.
Your second photo looks like the DS, I had to repair that side last year as well. It looks like not only the paint has cracked but the caulking has failed. On that side, I removed the caulking and caulked with a black caulking, and the touched up with touch up paint as it was a short area.
The joys of owning a motorhome
2018 Allegro Bus 37AP
2014 Phaeton 40 QBH (sold)
2022 Jeep JLURD