Well, I have not reached that point yet with modded Oblivion. After a couple years with vanilla Oblivion I may have almost reached that point playing about 10 to 15 hours a week on the average, and when Skyrim came out it was a welcome change. But my frustrations with Skyrim sent me back to Oblivion after about a year and then I decided I need to get a PC and learn how to use mods.
My modded Oblivion includes a whole new province in Elsweyr, significantly more complex and interesting cities with Better Cities, different and interesting landscapes to explore with Unique Landscapes, different and more interesting dungeons to explore with Snus Dungeons and Better Dungeons, complete game mechanics overhaul with Maskars, Enhanced Economy, Supreme Magicka, and Realistic Levelling, a ton of new guild quests with Guild Advancement and other guild quest mods Guild Advancement depends upon, a compeltely redesigned arcane university with Universitas Acarnorum, an Imperial Legion guild with Fort Akatosh Redux, etc. etc.
It will be several more years of playing ten hours or more every week to exhaust all of that new content, and once that happens, there will be a slew of new mods, not to mention the hundreds of mods I want to try that are not in my current load order, like Lost Spires, two different rebuilding Kvatch mods, new province mods for Black Marsh and Hammerfell, Ubanga, Integration the Stranded Light, TIE, OOO, Origin of the Mages Guild, just to name a few. There is a lifetime of content out there just in Oblivion mods alone, not to mention all the Morrowind mods like Tamriel Rebuilt and the upcoming Open MW.
Exactly.
Well, if you are making up your own stories then even the same content can yield vastly different results, but I understand what you are saying here. On the other hand, with mods, you may not know what's around the corner or through the next door because it may be different than what you expect from your unmodded game or even from your modded game with a different load order.