I can't offer a huge amount of advice, but i can tell you my experiences.
I jumped straight in the deep end. Skipped basic astronomy and dove straight into an 8" f3.9 newtonian on an AZ-EQ6 mount. Got all the bits and pieces to go with it too. Hooked up a Canon Eos 60D to it and away I went.
The learning curve was huge. Monstrous.... HOWEVER after spending a couple hours a day for a week or so on learning the gear, and setting up the software, and the lengthy courses on collimation and photography, I took the gear out and the first night i got some awesome quality pics. So the effort was worth it.
Thats just my two cents. If you have the time and patience, you CAN get there, so don't let yourself be scared off by the daunting learning curve ahead.
Plus there's plenty of advice and lessons etc on these forums from guys with decades of experience under their belt!!!