The extent to which one should do a wind-based plan depends on how much reserve you have and what cockpit instrumentation you have.
I have an aircraft with a 1300nm range (to dry tanks) and this makes the vast majority of flights within Europe doable with a big reserve. I also have a fuel totaliser (accurate to 1-2%) which is linked to a GPS and this displays a constantly re-computed "landing fuel on board" figure, based on the current GS, etc.
Put that together with a quick look at the MSLP chart to what kinds of winds aloft might be expected, and there is rarely a need to do a traditional PPL-style wind corrected plog.
Otherwise, if using a laptop flight planning program, there is no harm in putting in some sort of average wind figure...
Obviously, all this assumes that you have constant lateral track guidance i.e. GPS or VOR/DME. If one is dead-reckoning, one needs to fly wind corrected headings to have any chance of getting it right.
You will be unlikely in practice to fly to any greater degree of accuracy that a computer might give.
which is true even if you have a slaved HSI system and are flying a heading on an autopilot. If flying manually, with a typical knackered spamcan DI, a rule of thumb will be better than any accuracy a pilot can achieve.