Hey there! I have Tanna who is very similar to your own character. She is a bit of a 'nomad' and currently works with horses even though I plan on steering her towards the path of a bard/storyteller so I will help as best I can given what I have learned along the way.
To travel across any stretch land, especially from one city to another, it is
strongly recommended that your character has the Wilderness Survival skill and that you specify what sort of biome/environment that applies to (Tanna came from the Sea of Grass so I gave her Wilderness Survival: Plains to justify her being able to get from Endrykas to Syliras).
As for housing, I started with the tent housing package but I have her staying in
Traveler's Row while she is in Syliras proper because characters can earn a discount off their stay if they board there for the season. I'd recommend putting your character in some form of temporary housing while she is in the city to avoid the ire of the Order. Traveler's Row is probably your best bet while your character is in the city - that or you could have her stay in an inn like
The Broken Casket on the docks or
The White Swan Inn in the city.
As for work, she could either act as a 'bard' in a tavern or in the streets telling stories (skald might be a better word and it would help to build the busking skill - Performer/Bard/Busker - 4gm/day) or she could do something with her other skills such as trying her hand at crafting and selling as a Bower/Fletcher (3gm/day) or working with horses (Animal Handler - 5gm/day - you'd need to speak with the ST to see if it would be ok for the character to
only handle horses since this requires Animal Husbandry). I have Tanna working at the stables as a handler and intend on eventually building adequate skills to get her into the performing career (even though it earns less).
Hope this helps! Good luck!