Is there a way to add the following aspects to Skyrim using mods to make it more roguelike?

Perma-death? (I guess I can just not reload after I die and start a new game but I figured I'd ask)

More enemies?

Random starting location(I guess I could use random alternate start mod)

Random starting equipment/stats?

Random character generator? (or at least the option to randomize during character creation)

Any way to bypass the beginning of the main quest so you start with the basic shout?(still want to keep quests though I think)

Random loot?

Thank you in advance!

Search the Nexus for each of the things you list. Most of them have several options to choose from

Immersive Loot- nice additions for loot

Skyrim Unbound-choose where you start, starting equipment, choose if you want to be Dragonborn or even have dragons present

Alternate Start, Live Another Life-similar to above but you are still Dragonborn

More enemies- OBIS...Oragnized Bandits in Skyrim