Wow you packed alot of questions in there. Lets just dive in shall we:
1. Where would be a good place to start for the two of us?
An Antelope hunt is a very good and often succesfull hunt to wet your western hunting appetite. You can do these relatively inexpensively. You can stay in a hotel in some small town and drive out each morning. Its an excellent hunt for youngsters as there is lots of game to choose from and very little "slow time". You wouldn't need an outfitter for this. You can do a little research and find that there are several units in Wyoming that have nearly 100% draw success. Many farmers will allow hunting for a minimal fee.
2. Where is the best place to find a good outfitter?
Ask people who know. You can ask here and I'm sure folks will give you opinions. If you know an outfitter you can ask if anyone knows of them. If you don't have anyone in mind ask for us to recommend one.
3. Is an outfitter even neccessary?
Its certainly not necessary, but in many cases its sure makes life easier. Success rates increase dramatically with an outfitter. But, DIY is extremely rewarding.
4. What can I expect the $$$ extremes to be? I know that self-guided hunts can be cheaper and upper level lodges more expense. I hope for this trip to become an annual thing and want my other daughter and my wife (neither hunt) to be in a position to come with us. I would have to cater to them as well and would not be against renting a cabin or such for the hunt.
What are your finances like? Not to be nosey, but for an outfitted hunt your looking at a minimum of $3000 per person I would guess and the sky is the limit from there. So your looking at a minimum of $6000 per year for you and your daughter. If you can swing that then your golden. If your like me and that isn't an option, then you have to look into other options such as a do it yourself style hunt or going less often.
5. When is the best time to hunt?
During legal shooting hours. I mean come on buddy. We can't answer that for you. You must answer some for yourself. Archery increases your odds of drawing but also decreases your odds of success. So you decide on that one.