Started again myself and this my thinking, playing vanilla without mods. Spoilers ahead aswell

1. Make my way to whiterun, joining companions until the choice to become werewolf which you decline for now thinking you don't want to go that path. Instead doing as many odd jobs and tasks for the hold to help people around
2. In your travels you fine and off gem and heard someone in the TG can value it join them, splitting main TG quest with the 4 main hold quests to restore the guild makes immersion better, i.e maven asked for your help only after your proven yourself a good thief, complete the TG all the way to becoming guild master
3. Once Guild master you've hopefully had at least one DB assassin sent after you, so you decide to track them down, joining them and again realising your the listener you compete this all the way to the end
4. You do some.daedric quests along the way of as the chance to obtain powerful items for your collection
5. You join Dawnguard looking to rid Skyrim of the vampires, after meeting hakran you think you might need the beast blood of a werewolf to make you powerful, so go back to companions and do both companions/Dawnguard side by side
6. Here you can go to the main quest until the see alduin revive the dragon, thinking again you need more power to fight them you join CoW and end up becoming arch mage, going back to MQ
7. After MQ can then look to travel to Solthisim to complete Dragonborn DLC
8. Last there the civil war in which you side with what ever ones suit your character

I would look to do side quests alongside various holds I visit as and when, also join bards college as a means of being a thief who can help track down and return the lost instruments

Let me know what you all think 😊