I come across those kind of jobs from time to time.
The key is to NOT bridge the gap between the skirting and flooring. If you do, the expansion in the flooring will pull the caulk/etc away from the skirting.
Depending on the size of the gap, I run two layers of 1000 grade lining paper under the skirting. If the skirting is a reversible skirting, I use minimal expanding foam to create something for the filler to stick to. I cut away the excess foam and then use something like Toupret RedLite to fill down to the floor. Once that has cured, I sand and then pull the lower layer of lining paper away. I then cut through the upper layer of paper.
By using two layers of paper, at not point will the foam or filler be in contact with the floor. The floor is free to expand/contract without issue. You will end up with a 0.52mm gap at the end of the job.
More importantly, you will have a clean 90 degree between the floor and skirting. With caulks/polymers, you will end up with creep on to the floor.
I am in the middle of replacing cracked caulk with polymer sealant. Works better than any "pro" job. The pro clown job only lasted 2-3 months. Mine will do better.
Caulk doesn't "crack" (assuming that it was applied properly). Waterbased paints over some caulks however do crack. The extent is a factor of the caulk and waterbased paint used. A common mistake is to paint waterbased paints over the caulk before it has cured.
I seldom find that Everbuild 125 will crack when painted with Dulux Trade emulsion. On the odd occasion that it does, I hit the caulk with a shellac based paint. 25 min later I can use the emulsion over it.
MS polymers are great (CT1 etc) but they can be difficult to smooth. Additionally, they need to be primed with waterbased paints and if primed too early, the paint will crack.
100% of caulks in 2 houses and 1 flat were cracked. Also, anywhere else I looked where caulk was used in other people's properties. I don't install them. Something in the gut strongly deterred me even though I have many tubes of them over the years. I will now throw them all out. Life will be much better with one less irritant.
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