The hatches are fairly watertight, but not perfect. I once got into some really rough stuff when a storm kicked up on Lake P and had some serious waves breaking over the bow and the front compartments got a little water in them. But, in normal conditions I've never had a problem. I typically keep anything that needs to be dry in a dry bag since I'm yet to find a place in a boat that never gets wet.
I bought mine at Cajun Outboards too, from Toby. Good place to deal with and they gave me a solid price on my trade in.
Your upper body won't get wet, even in 3' seas, though your shoes might (see above). In 1' chop, you'll hardly notice. I honestly feel that my 1960 handles chop better than the 22' deep V Parker I also fish out of.
No other issues with the trailer, but I did add a few things to it. Namely, it didn't have a safety chain or transom tie downs, both of which I added. The tie downs make a noticeable difference in how it handles when towing too. Also got a mywedge for the motor, since the trailer doesn't have an easy way to put on a traditional motor support bracket.
No regrets in getting the 19' at all. Its been a great boat and its size makes it easy to handle in the marsh (I do a lot of inside fishing in the winter) and makes it easy to get into my carport at home. I've had 3 other people fishing with me numerous times and if everyone is competent, its plenty big enough for 4 people. My only 'regret' is that I didn't get the larger motor. Don't get me wrong, the 115 is entirely capable of pushing it well. But, with a 140, I bet you could easily break 50