Hello Mike,
Sounds like a very good project. I personally think for your price range the Davis is the way to go. I think you could hang your anemometer off your radio tower at 30' and add a transmitter kit to that. Site your ISS as best you can per
http://home.comcast.net/~dshelms/CWOP_Guide.pdf. (You are correct. Rooftop is not normally the preferred location.) To eventually get your data to the internet, you must get it into your computer which requires the "Datalogger". If you or a co-worker are computer savy, the WeatherLink program included with the Datalogger can be used to provide info to a website. I am aware of three programs for your consideration to make publishing to the web easier. The most popular (I think) is Virtual Weather Station, the most complex and best supported is Weather Display, and the most cost effective is Cumulus which is DonationWare.
Even if you go with the Davis 6152 which is < $400.00, by the time you have it installed and online, you will be close to you $1000.00 mark. That being said, more lives are lost to lightning in the US every year than any other weather problem so I would suggest you already start planning a follow up project of a Boltek Lightning detection system.
JMO
George