Are you members of your local astronomical society? If so you can 'try before you buy' by attending their public meetings to get hands on experience, and maybe borrowing one of their 'loaner' scopes to try.
An 8" dob is a good way to start learning the sky, quick to set up, easy to use, but not easily upgraded to tracking or goto later.
It will probably need collimating before use and checking thereafter to get the best from it.
Bear in mind it will come with only basic eyepieces and accessories. Better eyepieces, filters etc can be acquired as you go along.
A copy of 'Turn Left at Orion' is a sound investment with any scope and age group.
John.