Quick brain dump then.
OK - with regards to monitoring, the most important starting point is the desk. You need to have as many aux sends prefader as you want individual mixes. If your desk hasn't got enough sends, you are knackered from the word go as you'll be ending up sharing mixes or not having enough mixes to cover all the individuals in the bands requirements. Remember - a drummers wants from a monitor mix is very different from a vocalists... and so on. If at any point you want to go In Ears, remember you can now get stereo in ears, so you'll need twice the auxes for running up a stereo feed. In short, don't buy the wrong desk as you are usually stuck with what you get. (OK, digital desks you can expand some what from an I/O point of view)
With the advent of digital desks, aux sends are a lot more plentiful and configurable but there are still those that prefer an analogue desk. A digital desk has lots of pros and negatives but I fear that is a completely separate topic.
From an ease of use and carriage, powered monitors are the way to go. Make sure you don't buy weedy... depending upon the size of the venue, you'll soon find out that on the larger stages, you'll need some more umph if you plan on travelling any distance from your monitor. Additionally, ideally you want a bare minimum of two 31 band eqs, one for FOH mix and one for monitor mix to ring out any troublesome frequencies. This means outboard. Outboard means more carrying of gear. I don't know how serious you want to get, but ideally you should be carrying around some compressors, gates and reverb units as a minimum. Some analogue desks have reverb built in... I'm not sure of any that have onboard compression or gates... All of a sudden that expensive digital desk is looking more favourable - but having said that, I guess there are numerous bands out there who are running all the signals into the desk uneffected and applying a smidge of reverb at the backend before delivering the output to the FOH.