If you successfully play two characters at the same time any tips would be appreciated, or if anyone has any advice to give me as well.
I always run at least 4 different builds. Each has a purpose and each is enjoyable for different reasons.
No one character should do it all. That's not what a Single-player TES game is about.
Base types, though not locked in to hamper oneself:
1.
Male Nord Tracker/Cartographer. He lives off the land and doesn't do a single quest.
Not one. Wears Light Armour and wields a 1H Axe and Bow. He also utilizes a torch for blocking. Simply roleplaying as a bystander in the province, occasionally helping a local met on the roads, charting the province as he goes. Has a penchant for freeing any and all prisoners seen, then smiting the escorts no matter who. LOVE that guy.
2.
Male Bosmer Rascal/Fisherman. He's my rogue type, wearing only clothing and dual-wielding daggers. Good at heart but can't keep his mits off all those shiny baubles strewn about the world. In the Guild and does various Daedric quests.
3.
Female Breton Seeker/Healer. Walking her way around the Holds, studiously making her own charts of ingredient locales. She's my College Mage build focusing on Restoration. With only enchanted robes and clothing, a dagger rests on the hip for times when those with ill-intent come too close.
4.
Female Redguard Vindictor. This lass has a chip the size of Ysgramor on her shoulder. She works the MQ storyline and Companions with nary a minute to stop and take names. My tank build wielding a 2H blade.
It's YOUR game, so play it as you choose. To limit oneself is self-defeating, as is having one character do everything.
Sparse out the duties and interests and you'll always have a character ready to suit your current mood.
One person's opinion.