I haven't tried the Press board, but I have been riding Cable park and only rails / sliders on my Roam. It has no damages at all, and is super fun to ride. KEEP IT, KEEP IT, KEEP IT
I have a roam and love to play around on I can't do anything at all on it toeside but other than that besides my wakeskates it's the most fun board I've ever had
Keep the press because you can ride it with or without fins. It changes the feel of the board from a board you can butter on or rail slide all day or put the fins on and have a more of a traditional feeling wakeboard. Just my thoughts.
and to answer your question about the slingshot boots (four hole mounting) Yes it does help the flex, However it is Not necessary to enjoy and benefit from the flex. With this said, there is a reason that SS and Company wake primarily use 4 hole. To take get "greater" benefit from flex And to have greater boot to board security and response. Just so you know the numbers, You will lose about 4 to 8 total inches of flex potential with traditional bindings as to 4 hole mounted i.e. slingshot bindings (4 inches dead spot per slingshot boot vs 6-8 inches per traditional boot.)
slingshot offers traditional inserts as well (08 boards and beyond) that are individually laid which allows for better flex. most traditional board's inserts are laid into the board in sets on a plate, making the board more ridged. ---------------------------------------------------------------------------
In light your EXACT Original question i'd personally keep the press over the roam because you can put in fins and it is wider and will react better on the wake too... as has been said. And the graphic is better ;) imo
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