I have a DeWalt Cordless Air Inflator that requires very little effort to carry out to the bike, set the PSI, and inflate to that PSI. Much less effort than using a bicycle pump or even hooking up the Dynaplug Micro Pro Inflator I travel with, which is great because with those I would be more tempted to neglect tire pressure which can be dangerous. I end up checking the tire pressure about every 3 days or anytime the temperature drops significantly. I run the owner manual's recommended 25 psi front and 33 psi rear even with the Shinko SR241 2.75-17's. With aftermarket tires there's usually a different optimal pressure for each tire, but unless they state it for the specific bike the best you can do is guess. Running the manual's PSI for OEM tires is a good enough guess for me. I will sometimes air them down on longer offroad stretches of loose terrain, but not a lot since there's no rim lock.
On street bikes I often add the little Bluetooth TPMS valve stem caps to be able to check pressure more easily when I'm away from home touring.
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Update: I have since learned to run lower PSI on the knobbies, otherwise they wear prematurely at street level PSI, also they provide less traction at such high PSI. Lowest I've gone is 18 in front 25 in rear and that seems fine, usually running 20 PSI in the front and 30 PSI in the rear though and living with the tire wear since tires for this bike are cheap.