A skimboard/wakeskate is only fun in low wind days, definitely can't have it as a one board quiver.
I think skate is better when its >20 knots as for skim it does work well light wind but I have ridden into the 30's before, and my skate pretty much is my one board quiver. Good tips though.
Not hard to ride, just need to co-ordinate the kite with the board to keep you on it. Probably easier to learn on a twin tip, cause no need to think about what the board is doing.
I can't give you an objective opinion. Once you get used to riding strapless its very easy but learning the basics without straps would be harder for sure.
If you already own a wakeskate and skim, then get the basics down first on the twin tip, then mix it up with the other boards. TT has straps and fins so will be easier to learn on.
I am riding surfboard and skim only at the moment.
A Wake/Kiteskate is a great thing. I use it when i'm tired from doing unhooked tricks. Most people do skate tricks hooked, and therefore it's like a relaxing style after riding freestyle/wakestyle.
the naish alia is a bit of fun to break the boredome is very fast in light winds gets you out there on marginal days,feels like your skating on ice allthough ive never snow boarded i imagine its a simillar feel,got any old boots rowdy
A Wake/Kiteskate is a great thing. I use it when i'm tired from doing unhooked tricks. Most people do skate tricks hooked, and therefore it's like a relaxing style after riding freestyle/wakestyle.
Below you can see my kiteboard and my wakeskate:
How did you get a Driftwood in Oz? I thought they were only available in the US and UK.
the naish alia is a bit of fun to break the boredome is very fast in light winds gets you out there on marginal days,feels like your skating on ice allthough ive never snow boarded i imagine its a simillar feel,got any old boots rowdy 
