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It depends on the level of the gym, 1 trainer/mon per level, it starts at level 2 (but drops down to 1 or 0 if enough defeats happen). If your team has control of the gym, you can train there to get some XP and to help level up the gym.How many people can put Pokemon into a Gym anyway? Should I challenge one when I am Level 5 or better wait because there will be dozens of mons wanting to stomp me?
Also, challenging a gym after level 5 basically gets you a request to join a team the first time. Think VERY carefully about the team you want to join, the color of the gyms you see in your area.
Also, I've been noticing that the trainers in my area have been beating down gyms and stuffing weaker mons in the gyms. Also, depending on the type advantage/disadvantage, you can see pokemons with high CP being beaten down by a weaker pokemon (I've heard that depending on the difference and moves involved, you can see a strong pokemon being beaten by a weak pokemon with a 500 CP difference). It's HARD to defend a gym... so, you'll see gyms trade from team to team.
I'm only level 12, though. Since my game doesn't show me how close Pokémon are, I'm pretty much unable to actually hunt them down. I can only wander around randomly and hope they pop up in my path, so I haven't found very many.
In fact, most of my stronger Pokémon have come from eggs, since I get enough mileage each day to either hatch a bunch or get real close to hatching them. On a good day I can usually hatch a 10km egg and make good progress into a second one, but most days I make more like 8km. Makes me wish I had a second permanent incubator so I could hatch multiple 2-5k eggs at once.
It's a known bug where the proximity thing got turned off for some reason.
That said, while you can't see how close pokemon are... you CAN basically hang out in parks with multiple pokestops... typically, you'll find people gathering at such places and setting up lures to get pokemon to show up. I've also found that being in a bus or other forms of transit can help as you're basically moving about (even if you're going too fast for the eggs to count mileage, must be below 20 KM per hour).