ComputrNerd, telescopes are not like sweaters.: You buy a cheap one, and then replace it with a better one and the you buy another better one and so on....
You should save some money to buy a great (not literally) telescope, whic you are going to keep for a loooong time! Because when it comes down to it, after all those explorations, that money would be really worth it. So be careful, don't rush!
Consider all your options and make sure you do a "Pros and Cons" chart before you make your move.
At least that'* what I would do.