Hi apologies if these are dumb questions,

We are in Chicago,

I work remote for the US company (Analytics field) and also in the process of opening my LLC(had one before too doing ecom) and have an upcoming customer contract,

I have a proof of employment though it doesnt specify that I am remote,

Q1 will that be enough for Workation? Do I need to attach both, proof of employment and LLC/customer contract info?

Q2 in Chicago it only gives me option to apply online, so do I just attach all of it there?

Q3 I have a dependent, do i need a separate application for him? Do I file both at the same time? Attaching all the same docs for him?

TIA