That is the nature of low loss cable.
You can try heliax cable, but I beleive you will have simular problems with the connectors. Heliax is a wave guide cable so it is thinner by nature than the LMR cables, but more expensive.
You could try vasaline in the N-Male.. Carefull not to get any on the centre conductor.
You can also try a heatshrink with gel seal.
As far as the connectors, you might like the compression fitting better.
You have to try different things to know what your own preferences are.
Get the EZ N connectors for the LMR400. No soldering, just one crimp.
They come with a nice piece of heat shrink too.
I put my lightning arrestor where the wire goes indoors rather than on the tower.
Times makes ultraflex cable which is more flexible than regular LMR which might be handy for your jumpers. It is more expensive too, but might be worthwhile for those short pieces. Times would probably send you a sample for asking.