An update from MOO land. I finally found an Ebony Mace that I could use after running into a Bone Knight in Vilverin, of all places. I really didn't expect to find such good loot given how close it is to the Imperial City, but the spawns around the IC seem to be a bit screwy. It's like anything on the Imperial Isle is (rightly) considered low level, but as soon as you get to the other side of Lake Rumare, all bets are off. Shock Damage + Ebony Weapon is a hilarious combo for running Oblivion Gates, since Slayer damage combines with most Daedra's inherent Shock weakness to just make the whole experience ridiculously easy. Daedroth are going down in four hits. I also started doing Knights of the Nine, and decided that I would do the entire Pilgrimage quest without fast-travelling, and only stopping off at inns in order to sleep. No stops in town to re-stock on potions or hammers. That took about five in-game days, went across three play sessions, and ended up with about 30,000 gold worth of loot sitting in my horse's saddlebags from various overworld encounters, running a couple of dungeons and closing a few Oblivion Gates I came across. Alchemy + Armorer is a great combo for being totally self-sufficient for long periods, so combined with
Simple Horse Utilities you can spend more time dungeon crawling (maybe three at a time) and less time going back and forth between town.
Below is a rough map of my route, starting at Anvil and going along the road past Kvatch, resting the night at Gottshaw Inn. The next day I continued to Skingrad, and then took the wilderness track up along the
River Ethe Unique Landscapes module, before ducking into Weynon Priory to rest for the night and to start the KOTN-related quest mod,
A Posthumous Request. The next day was just picking mushrooms along the picturesque Orange Road, closing an Oblivion Gate and then resting at the Roxey Inn. The next leg of the trip was the long one, and the part that I knew would be most difficult, since the Nibenay Basin and Blackwood are generally one of the areas where you can reliably find difficult overworld encounters. The trip along the shores of Lake Rumare was uneventful, but shortly after the Wayshrine of Kynareth a pack of five Dire Wolves attempted to gang rape me, and I was really only saved by the fact that I'd managed to acquire two Reflect Damage items, so I could heal through the damage as they continually staggered me and basically let them kill themselves. I also got diseased. Twice. I stayed at the Imperial Bridge Inn before attempting to fight the Necromancers in Cadlew Chapel and traverse the mod-added caverns below, and after emerging, continued down the Yellow Road into Blackwood. It was getting dark, had begun running and I encountered a Baleful Spirit on the road. So far, this has been the only encounter that I have really just had to give up against. It damaged me too quickly most of the time, and on the off-chance that I did manage to kill it, it was only because it had been distracted by my horse, which always resulted in my horse being killed (usually by an AOE blast that took off half of my health) and 30,000 gold worth of loot now being stranded in the wilderness. I opted to run, and I have to tell you, running away from a pissed off cloud that you can barely see, in a swamp, during a pitch-black, rainy night is a surprisingly fun experience. I managed to lose the Baleful Spirit after crossing the rope bridge across the Niben River, and made it to the Wayshrine of Stendarr without further incident. There wasn't too much issue on this side of Blackwood apart from the occasional bandit or roaming Daedra, and I completed the rest of the pilgrimage without incident, coming across Sir Roderic and his squire just before I made it to the Wayshrine of Talos.
Obviously I would never recommend doing this in a vanilla playthrough. You'd spend the entire time fighting Ogres and Minotaur Lords and at no point would any of it feel interesting or eventful in any particular way. But with MOO, the overworld encounters are so much more varied and the feeling of danger as you get further away from civilization is genuine. I've mentioned in this thread that MOO's "encounter zones" can be a little bit wonky, but I think this was the most fun that I've had with Oblivion since I first played it fifteen years ago. In a game where you spend most of your time fast-travelling between towns and trying to avoid spending time in the overworld as much as possible, grabbing a horse and just going out to experience it is actually worthwhile as a change of pace and an experience in and of itself. Obligatory pretty screenshots below for all hiking simulator fans (warning, there's A LOT).