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Ok... let me start by saying I am a tech junkie. I worked in High Tech for a while at companies like Apple and AutoDesk so I have a whole lot of tech going on in my business... all the way up to custom created apps I use to do business
1) Both. I have a mac and a windows machine. I am migrating everything over to being Mac only tho. Even if your local MLS or association only has Windows apps for certain things, you can now use them on new macs as long as they are Intel based macs
2)I left windows because it was making me nuts. I found I had to reinstall windows about every 8 months because the system would start to slow down and exhibit some strange behavior. My mac has been a workhorse and has NEVER needed a system reinstall - and it has been 4 YEARS since I last did an system install.
3) My mac is pretty old (Grey and White G4 which I upgraded - getting new system in July). I built my windows machine from scratch, so parts of it are older than others. From a processor standpoint, its about 2 years old. I will also be building a whole new windows system later this year, but that will be for playing games ;-)
4) Software. Believe it or not, Microsoft Office 2004 for Mac is great - even better than the windows version. I have both the windows and mac versions and the Mac version is way better. There is also a new Mac version coming out later this year. If your looking for what your first purchase should be, it's Microsoft Office. The next most helpful has been the Adobe Creative Suite (NOT cheap). But it gives you EVERYTHING your going to need to get lots of stuff done. It includes, Photoshop, Illustrator, Dreamweaver, Acrobat Pro.. and more. With that tho, your going to be doing stuff with your website, print ads, creating digital forms, etc, etc etc.
5) SmartPhone and Laptop (TabletPC): I have the portable office thing going. I can fill out all our forms on my computer and print them out in my car with a portable printer. My phone needs to double as a way to get emails, etc. I was a big advocate of the Palm OS for smartphones, but I am not as up to date on that stuff these days as others.
6) Books. Well, there are so many out there. For realtors there is stuff like "Your first Year In Real Estate" by Zeller. I thought it was pretty good.
My suggestion would be to stick with the Mac as much as possible. Remember, I am a very computer literate guy. Hell, I was a tech support manager for both macs and windows and my windows machine could still make me pull my hair out. I have the skill to get my windows machine going and nursing it back to health, but the point is that with my Mac... I DON'T HAVE TO!
To get any windows stuff working, take a look at my blog, I did a post a while back specifically about this. There are two tools you can use to get windows stuff going on your Mac. One is "BootCamp" it is free from apple and will let you actually install windows on your Mac. When you boot up your mac, you can then hit a key to pick whether you boot in MacOS or Windows... cool. The other option is a program called "Crossroads" (not free), that does not even require windows to be installed to run windows apps... VERY cool.