This is a passion of mine, despite only being involved in 1 flight to-date.
First off, I think the best method of tracking is to use APRS: You will need to get an Amateur radio license, but APRS was designed for this sort of thing and there is a pretty decent existing network in the US available without doing anything on your part.
Our testing showed that a fairly low-power radio (we used both a 1watt HT and a 300mW on-board transmitter) will be picked up no problem once you hit a decent altitude (5k feet or so).
You'll be able track the payload at nearly all times (assuming you splurge for a decent GPS; $50 or less) without having any assets in the field using a site such as http://aprs.fi. The only issue is during landing - you may have issues due to the terrain blocking radio reception (we had a recovery team in the landing area that picked up the last couple of packets that lead us directly to the payload).
For example, go to http://aprs.fi and change the "Show last" to 7 days, then enter "KF7OHV-11" as the Callsign to track and click search. Note this only works until Brett uses the tracker again (since this data is months old), so the link won't work forever.
You'll see red dots indicating each beacon sent. Note the transmitter was transmitting once every 2 minutes (roughly), and every packet (save the last couple) was received by aprs.fi. You can also mouse-over and see that we had stations picking up our transmissions from hundreds of miles. Not bad for a non-tuned 1/4 wave home-brew antenna.
I used a custom-built APRS tracker board based on the Trackuino project (http://www.trackuino.org/). Nice, simple, and solid. It simply works.
All the eagle files and source code is provided (if you want my modified boards, send me a PM and I'll include them as well - I switched to nearly all SMT with a much smaller board - the flight version was 1.5"x2.5" and cost $130 or so, the latest version is 1"x2.75" and I got the cost down to about $100).
We weren't sure if 300mW would be enough power, but in the future the only reason we will mess with anything else is due to cost (the Radiometrix HX1 is $50 + shipping and I sometimes get older used HT's for $25 or so) or the desire to receive commands from the ground.
I hope this helps,
Brad (KF7FER)