Hey john I just did this, I have the dedicateds for Unix but decided to go with a reseller for Windows until I felt that I have mastered it I didn't want to full with any of the back end stuff just yet.
What did I look for in choosing the company I did, Good reputation, friendly staff, I called a couple times and they were quick to answer, didn't put me on hold for more than a couple minutes if they had too, customer forum was important to me as i prefer to look for answers on my own before submitting a ticket for support. My first e-mail to this company was that they implement a suggestion to make all the documents in pdf or printable format, I received a reply the same day and it was a very nice and personal reply not canned. Also the companyhad to offer the control panel I wanted to try which was h-sphere. Once I joined I found out this company keeps the customers informed of any and every thing that can effect the service and I appreciate that. Those were the things I looked for, I only wish this company offered dedicated because with service like theirs I would stay on indefinitely.
Name of the company I chose- Vortech Hosting