You're perfectly right. It would be wonderful if based on your skills, the game would randomly calculate some minor increases for things you are likely to use (Bowskill, Longsword Skill, Heavy armor skill) and then also give a chance to add to your inventory items you might pick up. This could be established in such as way as to create an interesting narrative for each of your travels, such as "You arrive in Winterhold. On your way you used 5 arrows, added slight wear to your bow, and gained venison." Or "Your arrive in Winterhold. On your way your Heavy armor skill increased, your Steel longsword received minor wear, and you gained 10 gold and a silver dagger." You can see how these easily represent their own adventures, such as hunting a deer or encountering a bandit.
I never said anything about getting random increases. You simply don't get anything out of fast traveling. Simply a quicker pace in time. Really, by fast traveling consistingly, you're only hurting yourself. As you don't experience the game, but if someone finds fascination from nothing more than merely fast traveling then I say, let them have at it. They're having fun with the game. The rest of us, can go on our epic journeys, discover that hidden fort with the really exceptional loot.
Besides, in Oblivion, while adventuring through, the wilderness and roads, I didn't encounter that much to be honest. Sometimes, I might have been better off if I had just fast traveled. Perhaps, you should be more concerned with what is out and about on roads and in the wilderness more than about a fast traveling system. Maybe spend more time, thinking of ways to IMPROVE the bestiary and wilderness via types of creatures, their placement, how they spawn, rather than bash the fast travel. Give players more incentive to want to go out there and explore that dangerous world seething with extradorinary creatures. Give people a reason to explore.
Also, I always get side-tracked in the Elder scrolls so it takes me a while to get things done usually, but sometimes I dedicated time to dungeon crawlings. Sometimes people just need to get to where they want to go. No questions asked.
I just don't get why you need a "fast travel" option when previous games already gave you transport along with teleportation spells and scrolls. The means to travel quickly (in the game and out of it) are already in place. I just feel it is another simplification. Is it tedious? Yes, but so is inventory management, and repairing weapons, and having to restore your health. They are the nasty little parts of the game that make the fun parts seem comparably more fun.
Also, Oblivion's problem was that because fast travel was so inherent to their system, they thought nothing of having the Fighter's Guild in Cheydinhal sending you on a mission in Anvil. Ridiculous. I NEVER had a problem traveling in Morrowind, either using the systems or walking. In fact, I LOVED the "journey" aspect of taking a silt strider to a port town, taking a boat to another city up the coast, wandering into the wilderness, getting lost, then hoofing it to some minor settlement to unload gear, repair and refresh.
But each time I tried to avoid using fast travel in Oblivion, I got INCREDIBLY frustrated, partially because there was no fast travel outside of the "menu teleport" so I was walking/riding everywhere, and because there was no mounted combat, I found myself dismounting every 2 minutes, OR leading a circus train of lions, tigers, and bears, OH MY. Nevermind the above problem of having quest which send you across the map.
Again, each player finds excitement by various means. Maybe some players desire that linear, "ok, you told me to do something, I want to get it done , right now, instantaneously" agenda where they want to just fast travel and complete the quest. So be it.
Maybe someone has a desire to look at the architecture in the cities and revel in it's marvel. Perhaps, someone wants to read up on some lore and check out some books. Each of which is scattered about. Maybe they don't feel like running around to get to these specific areas. Maybe they want to cut right in and get down to business. Maybe I'm in mood to avoid conflict, I'll explore the Chorrol mages guild hall and check out the city. I'll fast travel to do that.
It's the players' choice, not yours, not mine, not anyone but who is playing their game, it's their world when they're playing, not anyone else's.
Again, instead of bashing fast travel, think of benevolent and positive ways to help out transportation. Ways to make that better. Rather than leave it the way it is, and try to drag down fast travel, making two options more negative rather than positive in any way. What ways could transportation be better so I'm actually excited to use it? Better yet, think of ways to improve the quests so you won't need or want to use fast travel. Give people a reason to explore a quest, change some dynamics to make quests more fluid. Don't bash the fast travel system. I just ask, add improvements so that the desire for one to fast travels diminishes rather than malevolently demean a system which is there for those who use it with convience in mind. With great options, come great decisions. In the end, the player decides how fast travel is implemented, not anyone else. The option is put there for your use, however you may choose.