Recently I decided to get back into Oblivion after playing a lot of Skyrim, and I noticed a myriad of problems once I got into the game after installing. First is that when launching the game through OBSE, my graphics settings wont save and always default to medium quality (I'm also not forcing AA or HDR on). Second, even when I was in game my framerate would dip into the single digits sometimes, a real odditiy considering I can play Skyrim smoothly on High. I'm also getting a weapon draw glitch where when I try to ready my weapon, my character readies the weapon twice before I can actually use it. Lastly, even though I have installed weOCPS, I'm still getting a CTD on exit.

Here are my system specs:
CPU: AMD Phenom II x4 945
GPU: Nvidia Geforce GTX 560 Ti updated to the latest drivers
RAM: 8 gb DDR2

And here's a mod load order as well in case it helps (BOSS sorted):

Oblivion.esmCobl Main.esmOscuro's_Oblivion_Overhaul.esmEnhanced Daedric Invasion.esmBetter Cities Resources.esmHorseCombatMaster.esmUnofficial Oblivion Patch.espUOP Vampire Aging & Face Fix.espDLCShiveringIsles.espUnofficial Shivering Isles Patch.espBetter Cities .espSounds of Cyrodiil.espWindowLightingSystem.espClocksOfCyrodiil.espClocksOfCyrodiil_BC_OBC_OC_OCLR_Vanilla.espP1DseeYouSleep.espLiving Economy.espLiving Economy - Items.espXSPipeMod.espCobl Glue.espCobl Si.espCobl Tweaks.espOscuro's_Oblivion_Overhaul.espOOO-Water_Weeds.espOOO-Map_Markers_Stock.espOOO 1.32-Cobl.espFarmAnimalsofCyrodiil.espLetThePeopleDrink.espKnights.espEnhanced Daedric Invasion.espxuldarkforest.espxulStendarrValley.espxulTheHeath.espXulEntiusGorge.espxulFallenleafEverglade.espxulColovianHighlands_EV.espxulChorrolHinterland.espxulBeachesOfCyrodiilLostCoast.espxulBravilBarrowfields.espxulLushWoodlands.espxulAncientYews.espxulAncientRedwoods.espxulCloudtopMountains.espxulArriusCreek.espxulPatch_AY_AC.espxulRollingHills_EV.espxulPantherRiver.espxulRiverEthe.espxulBrenaRiverRavine.espxulImperialIsle.espxulBlackwoodForest.espxulCheydinhalFalls.espxulAspenWood.espxulSkingradOutskirts.espxulSnowdale.espxulCliffsOfAnvil.espxulSilverfishRiverValley.espxulJerallGlacier.espxulTheEasternPeaks.espSalmo the Baker, Cobl.espHarvest [Flora].espHarvest [Flora] - Shivering Isles.espDJ_Sewer_Hideout_01.espAlternative Start by Robert Evrae.espNew Arena v 1_2.espConduitMagic.espMidasSpells.espRenGuardOverhaul.espDeadly Reflex 6 - Timed Block with no damage or durability changes.espMounted_Spellcasting_Deadly_Reflex_Compatible.espSP1stPLegs.espBetter Cities Full.espBetter Cities - VWD of the IC.espBetter Imperial City.espDeadlyReflex 6 - Combat Moves.espCobl Silent Equip Misc.esp

Would really appreciate any help I could get. It's very odd to me that a game I used to play fine with what was an ok system for the time was fine, and now with a system that destroys the recommended specs I'm getting single digit framerates.

Somewhere in the back of my head is the memory of graphic settings not saving, but I can′t remember what it was. I think I reinstalled but I′m not sure..
Have you tried to play without OBSE or anything, just plain vanilla? Do the settings change then too?

Vanilla actually seems to work fine, so I guess its an OBSE issue, but I would have no idea how to deal with anything like that.

One thing that comes to mind is mod conflict. It′s tedious, but you could try removing the mods and adding them again one by one and see if you can pinpoint where it goes wrong.

Try playing with OBSE first though without any mods. Maybe it′s your version that somehow is corrupted.

Even running the game under OBSE with no mods installed, I'm noticing significant slowdown in any outdoor areas, even though my graphics settings are at the recommended levels. Are there any optimizations I should try, because I'm really confused why a system like mine is having trouble running a 6 year old game.

It's rather simple, really. Oblivion doesn't really make use of more than a single core on a CPU.

Also, get rid of the CPS. It's horribly outdated and causes a bunch of problems.

Wasn't aware of the problems with that, thanks for mentioning it (you can tell how long I've been away from Oblivion). As far as the CPU utilization goes, is there any way to work around that or should I just accept that I'm going to have to have a sub par experience with it? The more I think about it, the more it starts to sound like I should just forget about it.

Just gotta accept it, there aren't any workarounds there apart from rewriting the code itself. There are ways to mitigate the effect though, by optmizing meshes and such via PyFFI and/or NIFOpt to lessen the CPU workload, but the slowdowns will still exist due to the limitations.