I would have to recommend a vanilla playthrough first. Or even mid-playthrough, at least up to the point where you get bored and things get monotonous. I can assure you the chances are this will happen. Skyrim is a good game don't get me wrong, but it's not a great game. Mods make it a great game. A few things you will have to do though. You have to use the unofficial patches, you will be saving yourself a lot of frustration and hair pulling if you use them. Quests are bugged and these patches address a number of issues. You can also go for the texture packs they do no harm and don't change mechanics in any way, use these though http://www.nexusmods.com/skyrim/mods/607/? they are really good. There are a number of various brilliant texture replacers around too so if you feel comfortable you can look into those as well. As for modding gameplay, as I said first play vanilla for a while, eventually it will become dungeon/hack/slash repetitively. Once you get bored think about running through the various categories here on the nexus. At least now you will know and feel what has changed in the game and you can make an informed decision on whether you like the mod or not. If you do decide to use a lot of texture mods you will need to start thinking about memory capabilities and stability here are a few resources, I cannot explain all of them in detail would take to much time so look into the comments section for further info. http://www.nexusmods.com/skyrim/mods/38649/? <-----SSME Skyrim startup memory editor (memory related crashes) http://www.nexusmods.com/skyrim/mods/50305/? <-----ENBoost (expand Skyrim to 64 bit capability) These will help with crashing in general and particularly to memory crashing. So this is a good start and don't forget to enjoy the game and not get too carried away. When you do start modding do so wisely, read carefully into each mod and their compatibilities. use BOSS (next link) and add mods slowly one at a time to see if your game stays stable. http://boss-developers.github.io/ But most importantly enjoy the game! //thats the problem with a long post, this can now be regarded as an echo haha