Wow Oblivion, say goodbye to your social life...
Anyway, answers...
- The quest is very open-ended, so you can complete the main quest and still go back and do everything else. The difficulty of the enemies that you encounter changes depending on your level, so the game is always at a fair difficulty level. You can pretty much go through all of the guilds in any pattern that you want to, the games well designed in that respect.
- The Oblivion gates are repetitive, the only reason to beat them is for the treasure you may find. There are around 50 (i think) dotted around Cyrodiil, but you don't need to beat them all, but for levelling up purposes they do come in useful.
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