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Anthony, without wanting to rain on your parade may I suggest a different strategy? Buy a 10" Dob, better yet a second hand one, and three or four reasonable but not mega expensive eyepieces (e.g., plossls). Observe with this scope while saving money. Attend as many star parties as you can and look through other people's scopes and eyepieces. Hopefully by the time you've accumulated lots of cash you will have spent many nights observing and have a better idea of what kinds of objects you like looking at (e.g., do you like planets? The Moon? Deep sky objects?) and what kind of equipment is best suited for that kind of observing. A 10" Dob also fits into a car easily in two pieces (e.g., tube across the back seat and Dob mount in the boot) and can be picked up and moved around without too much hassle. Finally, after you've done some learning with the 10" and bought the huge scope of your dreams (or whatever it turns out that you really want) you can likely sell the 10" and recoup most of your money.
Happy observing whatever you decide to do!
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