Lastly, I appreciate the insights you offer but understand it is for those of a technical nature... when it comes to our personalities, mindset and approach to gaming I think we are totally different... I believe in risk reward, the more you push something the higher chances of it paying off in a big way but also of it failing... if I wanted to play it safe, I would never have even come to these forums...
I have to point out that risk/reward isn't often a great way to implement mods in Oblivion. As Psymon has stated, starting up the game does not equal success, oftentimes on-start CTD's are the easiest to trouble shoot, because often it simply comes to down to disabling mods until it works. Actually playing the game and encountering problems is a much more complicated process than disabling mods, which is why you need to know exactly what mods are affecting certain areas. Programs like TES4Edit can greatly help you out in many cases, like corrupted meshes or spawn points, because you can see which mod affects the cell that CTD'd you. However, it cannot detect scripting fallacies (to my knowledge), or tell you how much your computer can take before it starts crashing on you.
I just recently got a serious problem with Oblivion that caused me to reinstall the game, simply because I had so many mods that affected the game so drastically I couldn't tell what affected what in the game. At one point I had added 32 separate plug-ins to the game without playing once. Hell, for about a month, all I did was add mods to Oblivion, and I'd only play for about 15 minutes a week, then say "I'm bored. Let's add mods!" (Seriously.) and go download mods. I had close to 130 gb of downloaded modding material, around 40 gigs of which was actually in my Data folder. I added mods left and right and barely ever played, and a few days ago I finally stumped myself because of it. Too many mods. I can't playtest 30 different new mods and see exactly which one causes problems in certain areas.
We can't make you add mods slower, or play test the game thoroughly. But I am under the assumption that this thread was made because you wanted to create a vast, working, shiny new load order with plenty of ways to keep your Oblivion playing process smooth. And the fact of the matter is that in order to achieve that, you need to be careful. That may or may not mean playtesting every mod one by one and knowing every function (which we may seem like we're suggesting you to do. Rather, we know it's time consuming and tedious, and we know you don't want to do it). It means reading EVERY readme for EVERY mod, reading descriptions thoroughly (I'm not saying you don't but I have to say that it's important), adding them slowly (I don't mean one at a time, playtest each for 15 minutes and add another, I mean add 3-5 at a time, playtest for about an hour, have FUN, then decide what to do with the plug ins), and cleaning mods (another complicated process. Luckily many popular mod makers do this already.)
I know we seem like boring old timers, and it's not like I'm the most qualified to speak about this either. I only joined this forum in June, and I only first got this game last May. But still, it is considered common knowledge that Oblivion is like a high-class women. She wants quality merchandise (good mods), a willing provider that does all the work (you, spending your time playtesting and cleaning mods), and a suitable environment (a computer that can handle the mods). Don't beat her (add mods profusely and get mad when things fall apart), and don't get her to the point where she'll stab you with a rusty spoon (game-breaking CTD/reinstallation).
Point of my rambling: Huge mod lists that work perfectly are IMPOSSIBLE. There will always be issues, and the only thing you can do is try to prevent most of them. The game was not designed to do what many mods do to the game (just look at OBSE, or its plug-ins. That's essentially hacking Oblivion) and we're all determined to add a crapload of mods, which most of the time cannot be handled. Tread carefully, and try not to get stabbed with a rusty spoon.
/end rambling