The inventory menus are terrible, the gameplay is really outdated (though Skyrim's isn't that much different) and the voice acting gets very repetitive, but I still have some fun with it once in a good while. But it's typically not a good idea to play a successor before the predecessor. Going back to Oblivion after Skyrim made Oblivion's flaws even more glaring, and at times made the game very boring. Likewise with going to Morrowind after Oblivion, thus making it hard to truly appreciate.
Story-wise, it really doesn't matter with doing Oblivion before Skyrim aside from some references, sidequests, dialog, and books (but they're explained pretty well in the game). But having played the previous titles beforehand does make those quests and references more special. Skyrim in comparison to Oblivion is a case of out with the bad in with the good, and then some.