If you live in a suburban setting where the primary stars of the constellations are always visible on a moonless clear night, there is no reason why you should not consider at least a mid-sized telescope. But if you live rurally, where so many stars are visible as to make identification of constellations difficult—your budget is your only limit. Oftentimes it is best to wait and save for that extra two inches in aperture than regret not having purchased it.
With dark skies available just outside, any choice of equipment is a good one—from binoculars to a large dobsonian model telescope. More than anything, you need to examine your level of commitment: How often do you plan on using your telescope? What types of things are you interested in looking at? What size and weight of equipment are you willing to set up to view?
Choosing a pair of high quality binoculars, or a small to mid-sized telescope is a great stepping stone to learning. After having viewed a few things, you may find out that astronomy isn’t right for you. If so, your investment was only minimal and the equipment you purchased is durable enough to wait on your interest to peak again. If after some experimentation you find you want more—then your only consideration is your ability to move and set up a large telescope.
If you have a way of storing your equipment fully assembled, you’ll find you will use it more often. It is much easier to spend 20 minutes viewing a lunar feature if it doesn’t require 15 minutes of set-up. If a little caution is exercised, it is perfectly safe to move an assembled telescope—even a large one.
If skies are truly dark? Bigger is better!