Hi Matt and
to Ice in Space!
Before factoring in cost, you will need to consider your intended targets as different telescopes have different focal lengths and therefore frame subjects differently. Not to mention their differing setup and maintenance routines.
For example, there are large targets such as Eta Carinae, the Magellanic Clouds, regions in the centre of the MW especially that are spectacular in a wide field scope. Alternatively, a longer focal length instrument will so individual objects in those areas along with countless others dotted around the sky. The Universe is your canvas, but your choice of telescope will determine which subjects are framed best.