The straight tail deckover PJ comes with 6'-6" ramps, whereas, the dovetail comes with either 5' slide in ramps or 5' fold up ramps. That means that you have a couple of more feet of ramp length on the dovetail. This assumes you can fit all your stuff on the flat deck area. Based on my limited experience loading vehicles and tractors on this trailer, I think it would be a lot harder to load without the dovetail.
I just bought a 20 foot (17 flat, 3 dove) PJ 10000 lb, 6 inch channel deckover trailer. The options included fold up ramps and a spare tire mount and spare. Price was right at $4100, so your $3025 price sounds like a smoking deal to me....
Anyway, here are a couple of pics of mine.
That is a sweet looking setup you have there. The trailer I am looking at is not a deckover but is plenty wide for what I need. I have decided to go with the 20' flat. I have an area where I can load and unload on a slight slope that will take a lot of the angle out of the ramps. Then I don't have to worry about dragging the dovetail at the end of my road where it meets the county road. After looking at it closely, there was no way it was going to clear that spot without dragging quite a bit.
I am picking up the new trailer on Tuesday on my way back from Portland.
Ron