If I'm travelling Far and Remote (which tbh these days is the PW) I always Overpack Food and Underpack clothes. Clothes will remain clothes even if they smell sweaty and get a bit muddy whereas theres nothing more miserable than waking in a tent on a cold morning on the Fell with little to eat and little prospect of finding somewhere to get some. The advent of cars, Tesco delivery and shrinking village life means that long distance paths will never have enough places to buy supplies so I'll always take lightweight water-reconstituted food with me for a one meal a day hit - and if theres a luxury of a cafe, a shop or a pub then I'll stock up.
I always take a water filter - walking hungry is often necessary, walking thirsty is stupidity
I used to stockpile my old, nearly-knackered t-shirts and pants etc for long distance routes so I could just bin them when I'd worn them - these days sports-direct sell stuff so cheap and of a decent enough quality for hiking that you can squeeze them down and they're light enough to sit in the bottom of your rucksack until you can wash them out in the shower, and they dry quickly on a drying-room peg. Overclothes I spend more money on for the warmth, but again they stay warm when wet and are stupidly light compared to how they used to be.
Electronics-wise, I spend as much as I can on this stuff for regular use so when I need it for long distances it performs well - A top Android phone will usually take the best pics (no need for a camera so less weight) and will have the best battery (less need for a backup battery) and will perform other tasks quite well (music player, GPS, ViewRanger, nudey pics
, telly)
Good modern gear as above will repel water better, dry quicker and most importantly STAY WARM when wet
And finally. Most importantly. Marry someone who doesn't mind your daft hobbys and pastimes!! Having a partner willing to bundle the Labradors and a weeks provisions into the back of the car and then drive out 120 miles to drop it off at a particular road corner on a particular bit of moorland is a real benefit.
Roy