Hi, lurker here, but we're going through all this with my rising 4th grader, so here's my 2 cents:

We had to have an AT evaluation via the district to have the keyboard written into the 504. District assigned a NEO at the end of 3rd grade, but took it back over the summer. I was so annoyed I purchased a keyboard myself and had DS practice over the summer.

We ended up NOT getting a netbook for 2 major reasons: time to start up, easier to break. We probably will when he gets to middle school.

What we got was called a Fusion Writer. It is like the NEO (though more expensive), in that it is one button instant on/off, battery driven, very sturdy, very portable. It has other features we liked like on-board typing instructor, 'good writing' checklists, word prediction, audio readback, stuff like that. What I really liked was the calendar program... his school is big on kids having a written agenda and taking responsibility for due dates... but as you can imagine, a kid with dysgraphia writing down his homework assignments didn't really work out so well!

All of the portable keyboards I looked at were easy to use and all had USB ports to download files or hook up to a computer, and range in price from $150 to $300. About the same as a netbook, but I figure when DS is ready to upgrade to a net book, his little brother will get the Fusion.

With regards to guidance/structure, my 2 cents is plan on providing it yourself. The district was mostly useless, DS's school is willing but not experienced (DS is apparently first child to have a keyboard full time in the classroom). So I have been very active in making sure the equipment works, everyone knows how it is used, and DS is comfortable with it.

I am also not shy in asking about alternative ways for DS to do an assignment (example: Last year, DS had to do a 'scrapbook' on his state animal project, along with the essay. He typed the essay and did a powerpoint presentation for the scrapbook. He scanned all the pics in, designed the presentation on my netbook, and brought in a digital file on a USB drive and got to present it on the digital smart board to the class. I loved it because he got to be the 'cool' kid with the neat techie tools instead of the nerdy kid with the crappy handwriting!)

Hope that helps a bit.