I upgraded from a reseller to a VPS earlier this year - admittedly this was on the Linux side not windows. The learning curve wasn't steep at all, and VPS support have helped greatly when it got a bit uphill. The advantages (for me) are more space and bandwidth - being able to create packages with unlimited space/bandwidth (no more juggling resources at the end of each month) - having more control over the software running (eg I wanted php5 and with the vps it was done quickly and simply, with a reseller it meant a server move with all the hassle that entails). I have ssl for one of my sites and the charge is the same as it was for having it on the reseller (£39 or so I think - someone from EUK will know the exact figure), it uses one of the 2 ip addresses you get with the VPS.
Hope this helps you decide
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