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https://www.nexusmods.com/skyrimspecialedition/mods/12253/?
Good way to start a playthrough IMO.
Did you know? The legions always looking for strong warriors. If you are interested you should talk to Rikke at Castle Dour*.
*I do not endorse or support the Imperial Legion. I was paid for this Recruitment advertisement.
I concur it gives you some head start ... Guildhouse build, explores recruited, etc.
Get the quest from the smith. Get the quest from the White Phial.
Exit Windhelm and harvest wheat from the farms to the East of the stable. Go back to the stables and follow the closest road to the South. You'll eventually see a map icon for a village. Go there and do stuff. Leave and go back South or just head out towards a location that gets your interest. If possible follow someone or a group you can use as a human shields. Then just bebop along the road harvesting ingredients until you figure out what direction your play through will take.
If you're not starting the main quest, try to survive until level 9 and build Lakeview Manor so you have a place to store your crafting materials and other items you don't want to sell.
Or get the mod Shalidor's Staff and just explore. I've ended up in Riften before ever getting to Whiterun.
Very keen to try Legacy but not sure about the guild master start. Think I would like to play it from scratch. One of the things I love about Skyrim is starting out from nothing and gradually building a character out of the resources and activities the game world provides.
My outline for my character is I am a Breton arriving in Solitude from High Rock. High Rock Scout is a custom class I put together for an Oblivion playthrough years ago. He's a sort of arcane warrior. Light armor & weapons and arcane support. A sort of Jack of all trades.
I did not test this but I found something quite suiting for your playthrough though not exactly it.
In one of the alternate start add-on this one has is that you're travelling into skyrim as a merchant or mercenary. The rest if up for your RP! Not sure where you'd start but it's written that you'd start at the borders as if you just entered Skyrim!
https://www.nexusmods.com/skyrimspecialedition/mods/4939