2) Merged plugins obey load order just like active mods.
3) The older date on the optional modules just means that they have not been updated since that version. That is fine then.
4) Is your load order working now? It looks all right.
Active Mod Files:00 Oblivion.esm01 All Natural Base.esm [Version 0.9.9]02 Oscuro's_Oblivion_Overhaul.esm [Version 1.34]03 Mart's Monster Mod.esm [Version 3.7b3p3]04 Mart's Monster Mod for OOO.esm [Version 0.9.9MB3]05 Progress.esm [Version 2.2]06 nVidia Black Screen Fix.esp [Version 1.0.0]07 Unofficial Oblivion Patch.esp [Version 3.2.4]08 UOP Vampire Aging & Face Fix.esp [Version 1.0.0]09 Oblivion Citadel Door Fix.esp0A Oblivion.esp0B All Natural - Real Lights.esp [Version 0.9.9]0C All Natural.esp [Version 0.9.9]0D All Natural - SI.esp [Version 0.9.9]0E All Natural - Atmospheric Weather System.esp [Version Final]0F Natural_Water_by_Max_Tael.esp10 WindowLightingSystem.esp11 SoT_Holiday.esp12 Living Economy.esp13 Living Economy - Items.esp14 Cutthroat Merchants.esp15 Oscuro's_Oblivion_Overhaul.esp [Version 1.34]16 Mart's Monster Mod for OOO.esp [Version 0.9.9MB3]17 Mart's Monster Mod - Additional Enemy NPC Vars.esp [Version 3.7b3p3]18 Mart's Monster Mod - Gems & Gem Dust.esp [Version 3.7b3p3]19 Mart's Monster Mod - Hunting & Crafting.esp [Version 3.7b3p3]1A Mart's Monster Mod - Looting NPCs & Creatures.esp [Version 3.7b3p3]1B Mart's Monster Mod - Less Rats.esp [Version 3.7b3p3]1C Mart's Monster Mod - Less Reavers.esp [Version 3.7b3p3]1D Mart's Monster Mod - Safer Roads.esp [Version 3.7b3p3]1E Mart's Monster Mod - Spawn Rates - Reduced.esp [Version 3.7b3p3]1F Mart's Monster Mod - Dungeons of MMM.esp [Version 3.7b3p3]20 Mart's Monster Mod - More Wilderness Life No Gates.esp [Version 3.7b3p3]21 Mart's Monster Mod - Extra Wounding.esp [Version 3.7b3p3]22 Mart's Monster Mod - Farm Animals.esp [Version 3.7b3p3]23 Mart's Monster Mod - Diverse WaterLife.esp [Version 3.7b3p3f]24 Mart's Monster Mod - Slof Horses Complete.esp [Version 3.7b3p3]25 Mart's Monster Mod - Diverse Runeskulls Loot OOO.esp [Version 3.7b3p3]26 Mart's Monster Mod - City Defences.esp [Version 3.7b3p3]27 Kyoma's Journal Mod.esp [Version 3.2.0]28 Enhanced Vegetation [150%].esp29 RealisticFatigue.esp2A Pestilent Afflictions.esp2B StealthOverhaul.esp2C ZumbsLockpickingMod - OBSE.esp2D ProgressGSD.esp [Version 2.0]2E ProgressMBSP.esp [Version 2.0]2F ProgressSBSP.esp [Version 1.0]30 ProgressRBSP.esp [Version 1.0]31 ProgressRacial.esp32 ProgressArmorer.esp [Version 1.0]33 Mart's Monster Mod - Resized Races.esp [Version 3.7b3p3]34 OMOBS.esp [Version 1.0]35 OMOBS Optional Combat Settings.esp [Version 1.0]36 Mart's Monster Mod - Friendlier Factions OOO.esp [Version 3.7b3p3]37 Mart's Monster Mod - More Passive Wildlife.esp [Version 3.7b3p3]38 Mart's Monster Mod - Safer Quest Locations.esp [Version 3.7b3p3]
Active Mod Files:00 Oblivion.esm01 All Natural Base.esm [Version 0.9.9]02 Oscuro's_Oblivion_Overhaul.esm [Version 1.34]03 Mart's Monster Mod.esm [Version 3.7b3p3]04 Mart's Monster Mod for OOO.esm [Version 0.9.9MB3]05 Progress.esm [Version 2.2]06 nVidia Black Screen Fix.esp [Version 1.0.0]07 Unofficial Oblivion Patch.esp [Version 3.2.4]08 UOP Vampire Aging & Face Fix.esp [Version 1.0.0]09 Oblivion Citadel Door Fix.esp0A Oblivion.esp0B All Natural - Real Lights.esp [Version 0.9.9]0C All Natural.esp [Version 0.9.9]0D All Natural - SI.esp [Version 0.9.9]0E All Natural - Atmospheric Weather System.esp [Version Final]0F Natural_Water_by_Max_Tael.esp10 WindowLightingSystem.esp11 SoT_Holiday.esp12 Living Economy.esp13 Living Economy - Items.esp14 Cutthroat Merchants.esp15 Oscuro's_Oblivion_Overhaul.esp [Version 1.34]16 Mart's Monster Mod for OOO.esp [Version 0.9.9MB3]17 Mart's Monster Mod - Additional Enemy NPC Vars.esp [Version 3.7b3p3]18 Mart's Monster Mod - Hunting & Crafting.esp [Version 3.7b3p3]19 Mart's Monster Mod - Looting NPCs & Creatures.esp [Version 3.7b3p3]1A Mart's Monster Mod - Less Rats.esp [Version 3.7b3p3]1B Mart's Monster Mod - Less Reavers.esp [Version 3.7b3p3]1C Mart's Monster Mod - Safer Roads.esp [Version 3.7b3p3]1D Mart's Monster Mod - Spawn Rates - Reduced.esp [Version 3.7b3p3]1E Mart's Monster Mod - Dungeons of MMM.esp [Version 3.7b3p3]1F Mart's Monster Mod - Extra Wounding.esp [Version 3.7b3p3]20 Mart's Monster Mod - Farm Animals.esp [Version 3.7b3p3]21 Mart's Monster Mod - Diverse WaterLife.esp [Version 3.7b3p3f]22 Mart's Monster Mod - Slof Horses Complete.esp [Version 3.7b3p3]23 Mart's Monster Mod - Diverse Runeskulls Loot OOO.esp [Version 3.7b3p3]24 Mart's Monster Mod - City Defences.esp [Version 3.7b3p3]25 Kyoma's Journal Mod.esp [Version 3.2.0]26 Enhanced Vegetation [150%].esp27 RealisticFatigue.esp28 Pestilent Afflictions.esp29 StealthOverhaul.esp2A ZumbsLockpickingMod - OBSE.esp2B ProgressGSD.esp [Version 2.0]2C ProgressMBSP.esp [Version 2.0]2D ProgressSBSP.esp [Version 1.0]2E ProgressRBSP.esp [Version 1.0]2F ProgressRacial.esp30 ProgressArmorer.esp [Version 1.0]31 Mart's Monster Mod - Resized Races.esp [Version 3.7b3p3]32 OMOBS.esp [Version 1.0]33 OMOBS Optional Combat Settings.esp [Version 1.0]
Active Mod Files:00 Oblivion.esm01 All Natural Base.esm [Version 0.9.9]02 Oscuro's_Oblivion_Overhaul.esm [Version 1.34]03 Mart's Monster Mod.esm [Version 3.7b3p3]04 Mart's Monster Mod for OOO.esm [Version 0.9.9MB3]05 Progress.esm [Version 2.2]06 nVidia Black Screen Fix.esp [Version 1.0.0]07 Unofficial Oblivion Patch.esp [Version 3.2.4]08 UOP Vampire Aging & Face Fix.esp [Version 1.0.0]09 Oblivion Citadel Door Fix.esp0A Oblivion.esp0B All Natural - Real Lights.esp [Version 0.9.9]0C All Natural.esp [Version 0.9.9]0D All Natural - Atmospheric Weather System.esp [Version Final]0E Natural_Water_by_Max_Tael.esp0F WindowLightingSystem.esp10 SoT_Holiday.esp11 Living Economy.esp12 Living Economy - Items.esp13 Cutthroat Merchants.esp14 Oscuro's_Oblivion_Overhaul.esp [Version 1.34]15 Mart's Monster Mod for OOO.esp [Version 0.9.9MB3]16 Mart's Monster Mod - Additional Enemy NPC Vars.esp [Version 3.7b3p3]17 Mart's Monster Mod - Hunting & Crafting.esp [Version 3.7b3p3]18 Mart's Monster Mod - Looting NPCs & Creatures.esp [Version 3.7b3p3]19 Mart's Monster Mod - Less Rats.esp [Version 3.7b3p3]1A Mart's Monster Mod - Less Reavers.esp [Version 3.7b3p3]1B Mart's Monster Mod - Safer Roads.esp [Version 3.7b3p3]1C Mart's Monster Mod - Spawn Rates - Reduced.esp [Version 3.7b3p3]1D Mart's Monster Mod - Dungeons of MMM.esp [Version 3.7b3p3]1E Mart's Monster Mod - Extra Wounding.esp [Version 3.7b3p3]1F Mart's Monster Mod - Farm Animals.esp [Version 3.7b3p3]20 Mart's Monster Mod - Diverse WaterLife.esp [Version 3.7b3p3f]21 Mart's Monster Mod - Slof Horses Complete.esp [Version 3.7b3p3]22 Mart's Monster Mod - Diverse Runeskulls Loot OOO.esp [Version 3.7b3p3]23 Mart's Monster Mod - City Defences.esp [Version 3.7b3p3]24 Kyoma's Journal Mod.esp [Version 3.2.0]25 Enhanced Vegetation [150%].esp26 ProgressGSD.esp [Version 2.0]27 ProgressMBSP.esp [Version 2.0]28 ProgressSBSP.esp [Version 1.0]29 ProgressRBSP.esp [Version 1.0]2A ProgressRacial.esp2B ProgressArmorer.esp [Version 1.0]2C Mart's Monster Mod - Resized Races.esp [Version 3.7b3p3]2D OMOBS.esp [Version 1.0]2E OMOBS Optional Combat Settings.esp [Version 1.0]