Wasn't all that long ago that I was asking myself the same questions.
I chose to buy a set of binos. (11 x 70)
I started to learn what I was looking at and decide if I really wanted to go down this path.
After a few months of using the binos, I decided to buy a scope.
At this time, with a little more experience and reading just about every thread on the IIS forums, I decided that I wanted to view objects and that a dob was the way to go with a limited budget (bang for bucks)
I initially chose an 8" dob from Bintel, not for any other reason than that Bintel was easier to get to and an 8" is easier to transport.
After waiting for a number of weeks for stock to come into the country, I chose to upgrade to a 10" dob.
Bintel threw in a few filters for the inconvenience and the scope was collimated prior to collection.
This unit will still fit in the back seat of the car.
I admit that the eyepieces supplied are not great but they do provide an acceptable view for those starting out. (My kids think that it gives million dollar views)
I have since purchased a 2x Barlow and am saving some dollars for a couple of nice eyepieces (size and type is yet to be decided).
Try to get to an astronomical society viewing night and check out the scopes as people will be more than willing to help.
My advice is take your time, do your homework and you will not be disappointed and own an overpriced dust collector