I think they're getting easier. Some examples from the most recent generations:
1. Nurses/doctors. In the past, if you wanted to heal, you either had to spend money in advanced to buy lots of potions *or* go all the way back to the Pokemon Center. Most people did the latter to save money, but now that you have convenient healing in the middle of routes, you have an option which saves money and time.
2. The newer games have more options for level grinding, along with higher leveled opponents. This is one of the few made-easier things which I appreciate, because only playing against the Elite 4 (stuck at the same levels) over and over got dull.
3. In Black/White 2, did anyone notice that the prices for all battle subway items got cut in half than they costed in any previous games (including Black/White)?
4. Pokewalker and Poekmon Dream World give you level-ups much more easily. Especially the Dream World, which only requires 500 dream points regardless of whether your pokemon is lv5 or lv99.
5. We recently got free shiny legendaries through events. Getting legendaries for free has been a thing since GSC, so it wouldn't be a big deal except, y'know... these were already at lv100.
6. Not that levels are that are that important nowadays anyways... ever since Generation 4, we've had flat battles, which automatically make pokemon at either level 50 or level 100. A good option, don't get me wrong, but it defeats the point of having lv100s.
7. In Black/White, we got Lucky Eggs for free in the middle of story mode. No need to hunt down some 1% Chansey thing.
8. Black/White's Elite 4 only had less pokemon than in other games.
9. If you accidentally faint a legendary, it respawns.
I think a lot of these are good ideas; for instance, the last one, because some new players aren't familiar with saving before talking to a legendary, basically this doesn't punish people just for being new to the game. Anyways. Can't think of any others from the top of my head.