When I started with Hostwinds I had an intention to grab smallest VPS, but started with shared hosting account, because I was told I would be able to upgrade my account to VPS with no problem. And after some time I do understand that it was correct to not to start with VPS.
Signing up process - nothing special, but my new order was put "on hold", so I had to reach hostwinds and just confirm my identity. Do not feel really comfortable on this, but it seems to be normal to most services I used.
Now I have everything I expected (nothing extra) - site up and running, assistance always in pace (I always have the chat assistance when I'm in my client area).
Price I pay is fair enough.