If the set-up process is a taxing ordeal, you are less likely to have the motivation to get outside and use it when the clouds finally part at 10 pm on a Saturday night.
I would highly suggest a telescope that can be easily transported and set up in a reasonable amount of time.  If the set-up process is a taxing ordeal, you are less likely to have the motivation to get outside and use it when the clouds finally part at 10 pm on a Saturday night.