This is just some random thought, on the contributing factors when buying an equipment, in particular to those who have been playing for several years. To name those important factors, we have:-
1. Purpose: what will be the main purpose for the instrument? this is very important, a versatile equipment will be great, but versatility should be placed after the main purpose. be in for imaging, for visual observation, for quick grab and go, it got to be defined first.
2. Portability and Accessibility: whether the equipment will be useable for many occasions? where you can set it up easily? yes, we all want a 30" dobsonian, but it's not going to be your most used telescope; yes, we all want a 8" apochromatic refractor, too... I'd say, if one still does not own such a always accessible equipment, one should start hunting for one.
3. Price and Quality: this is by far the simplest dimension, simply go for the best which you can afford.
For my case, (2) is the most important factor.