We've done it for our show ski site. We do 3 shows each summer that are all sellouts. There is something very special about both skiing and watching skiing at night. Skiing is way cool because of the sense of speed. Watching because of the lack of distractions in the background. Your focus becomes locked on the person on the water. Very cool.
The biggest and absolute first consideration has to be power. You need lots and then maybe a little more. We put in a 400 amp service that is split into two 200 amp pedestals, one North, one South. Most of the stadium lighting comes as a triple tap setup. Go with 220 and you will cut the amps for each light in half vs 120 volt.
Second consideration is poles. We were fortunate to have a tree lined site so we put platforms up in old growth trees with some minor limbing. Figure at least a 50 foot elevation and placement to keep the lights out of the drivers and skiers eyes. Talk to your power company and their subs for pole installation. Usually somebody has a supply of used poles that will work just fine. Plan your light installation out and rent a 4x4 two person man lift for the install. The lights are pretty heavy and you need a second set of hands to do it efficiently.
Wire, bigger is better and run 220. There are several online electrical calculators that can tell you line loss and what size wire you need for the length of the runs. Watch the price of copper and you can do it for a fairly reasonable cost. Talk to electrical distributors, make a friend and they will sometimes do it for cost. Trenchers, walk behind self propelled units, can be rented for less than a hundred bucks a day and it is amazing how much you can do in 6 hours.
Lights. 1000 watt, metal halide stadium lights. Start with one at each position and then add them as required to fill in dark spots. There are multiple ways to acquire the lights. Keep an eye out for local schools upgrading. Check with electrical distributors and tell them what you are doing. Ask them to be on the lookout for any units that are basically "scratch and dent". People will be amazed when you tell them what you plan on doing. We I did ours everyone I talked to outside of the skiing world thought this was so "out of the box" that they jumped on board and have been super supportive. Lots of great advice and help form professionals. Hey Jim I found a light, hey Jim I found some wire, still happening today. There is a revolution coming in lighting and as new very efficient lights become available schools, stadiums will be upgrading and more used lights will become available. LED's are the next wave and when they get all of the bugs worked out everything else is going to be obsolete (just my non-professional opinion).
Take your time and make it fun.