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I'd suggest a trip to a local astro club public night (or join a local club and go along to a few nights) - have a look through a few of the scopes and different types - and try to gauge an insight into what you might be interested in looking at - different scope types are good at different things... visual/imaging and planetary/widefield etc.
It's a good try before you buy, and may give you an idea of what you want to 'scale up' to eventually if at all.... but it would be hard to go past a eq6 pro and small refractor as a start point, with significant scope (excuse the pun) all the way into medium duty imaging... there are a lot of people on here doing some fantastic work with eq6pro's - great bang for your buck.
It's a bit of a leap from a drop and go meade lightswitch which has the advantage of requiring very little sky knowledge to get up and running and take a tour - but has some very big limitations towards imaging etc - and IMO will be quickly relegated to the corner if you want to take photos etc.
Jamie
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