RE: EVO recommendations..
JOrdanwd, do you happen to know about what volume your old board had? If it was somewhere between 80 and 90 and you thought it was OK in size, chances are you would be better off with the EVO 80. The 80 has a bit more "drive" in the turn and handles speed very nicely. The 80 can still handle 5.7 even at your weight with an appropriate fin and for performance wave sailing the 80 probably is the best compromise (even though you will be struggling a bit on the light end).
If you want some reserve volume and an easier time in light and gusty stuff, the 90 is it. I don't think you need to worry about it not being loose enough since it is a very loose board.
As for comparasion in feel to your old board, its hard because I don''t know how your old board sailed. The EVOs generally have quite a lot more rocker than modern so called classic boards and hence "surfs" better, but in 99 most dedicated wave boards also had lots of rocker. The difference with the EVO is that it is so much easier and stable. Overall, if you're used to a wave boards from 99, I don't think you will have any problems getting used to an EVO. It's probably harder to go from a fast rockered modern wave board to the EVO since then one might be used to the kind of directional feel of such a boards and might have trouble adapting to the surfier EVO feel.
Please ask again if you want more info. I'll try to get some heavyweight to comment to.