I used to ride in Maryland with some of these guys, the Bay is different riding. You usually find a 45+ Viking or Hatteras and chase it for about a mile as it comes or goes from the marinas (we literally wouldn't move for any boat under about 35ft). They put up a consistent 4-5ft wake right behind the boat, more if the guy decides to be cool and drag some ass for you, you cross the wake then pin it full throttle to keep up with the boat while waiting your turn to cross the wake again and on busy and windy days the bay can get quite choppy. It's a ton of fun and you stay out for hours. It's not really flat water riding and its nor really surf something all its own that needs a special ski(but these guys usually do about 5-10 days a year at the beach too)
Even for smaller boat chasing I'd want something stable, light and not too twitchy or nose high. I had a 04 SXR that I paid $2500 for, and wanted a lighter and shorter ski that I could throw around a bit better (I'm 5'5" and 150lbs... rider size is one thing that people don't take into account enough). I ended up with a ROK because at the time it was one of the few SXR based skis. It had alot of teething pains after the build to get it to run right (took me almost 6mo and I'm still sorting things out and tuning). Even though I never rode that ski in MD, I can say it would be great for that kind of riding... literally is a shorter, wider SXR. The other thing to consider is getting something that can fit a 4+ gallon tank, a 2gal go kart tank just won't do.
That said, would I do it again? Probably would buy a prebuilt AM ski with a Yami drivetrain, much less of a pain in the ass (random things don't work... like I had to dent the poop out of my wetpipe to clear the hull and gas tank) and cheaper in the long run. I'd also pick a different vendor to buy from.
That and take everyone's advice and ride a few hulls a few times (after you think you've decided ride again). Don't know if anyone has a FR yet there, but they are worth a try as are things like the Trinity Evo, JB1, FP1, FR2. If the longer Trendsetters hull comes out soon that might be cool too.
There are quite a few AM hulls in the area, post up on the Delmarva Freeride facebook page and I'm sure the'll let you try.