As the longest continuing mapper in Edge Gamers I can say that just because you play the game, doesn't mean you can map or mod for it.
Hammer is a not an easy to learn editor and takes many years of practice to get better and better.
As for Jail requirements:
They must not break eGO rules (no swearing, nudity, racism, etc on the map, songs, models, textures, etc)
It should be 50mb max uncompressed (a little over is fine)
It should have VBSP, VVIS, VRAD all ran on normal
HDR Lighting is optional as sometimes it doesn't fit the map
It should not crash the clients or the server
It should not be FPS laggy or network laggy aka Optimize it
It should not use others' works unless you have received permission to use them