if it was me i would deffinetly clean and repack both bearings from my experience unless the cap is really loose to begin with the only reason it would come off during travel is because of heat from possibly a bad bearing when the bearing starts to heat up it'll build up pressure and poof there goes the cap. better to be safe then sorry
i killed a spindle once and it'll never happen again i clean and repack them every year especially if i know where going to be going on a longer trip then usual
TV 1997 GMC SUBURBAN, 92 Mustang Rag Top
PUP 1992 Starcraft Starburst
Eric 32,Tammi 37,Anthony 12,Julia 10,jason 9,Briana 7,Ashley 5,Robert 2
Dave, the advice about using a prick punch from the inside to carefully peen out some dimples works well. Another trick in case you find a tight one (the manufacturing tolerances are all over the place on the holes in hubs and the stamping for dust caps, or you go too far with the punch) is to buy a pipe nipple that will just slide over the central part of the cap and rest on the flange.
It allows you to drive the cap on straight and not dent it so it won't fit.