First, the A20 is a great boat, and since you are coming from a prostar 190, it will feel huge to you.
1. The 335 is bomb proof, it gets incredible gph ratings, and is plenty of power for almost any amount of weight you plan on adding. The bigger motors are rare to see in the A20 because it really is not needed. Although it has the TBI style intake and that ='s inefficiency to you, it is really not the case for this motor, relatively speaking. I consistently get 3.5 gph on my A22 with the 335 CAT motor and a whole lot of weight. It really is a great and efficient motor. I have heard of 5 gph's for most other motors, 8-10 in the old stars (04-11) and up to 15 in the new G series nautiques. I would chose the 335 if I had the choice between that and the 350 or 400.
2. Yes you can. You could redo most of it, changing the 2 rear tank pumps (4 total) to the 1200 gph and going with the large diameter hoses, leaving the centers alone (the stock ones are fine for that 400 tank), and adding 1200's fill and drain pumps and a thru hull up front for the bow bag. OR you could just upgrade the center pumps and hoses, and overflow out of that tank to the bow sack (this would take a long time probably and you would no longer be able to fill the bow sack without first filling the hard tank). The rear pnp option was nothing more than extra hose and extra anti siphon valves. That option from the factory was really only good for the front sack pumps, hoses, overflow and drain holes, and wired in rocker switch.
3. Your pro star is a super light boat. The A20, although only a foot longer, is probably close to a foot wider plus the wide bow, and probably weights and additional 1000 lbs over your prostar (just a guess). Add in all the extra gear and equipment you can put in this bigger boat plus any lead you will probably be adding to it, you have a way heavier boat than a dd ski boat. The tandem trailer is not a necessity but it is nice if you tow a lot.
4. Ive got nothing. I see so many aftermarket surfgate systems being added that you should be able to add it later if you need it for a reasonable price.
Every year they seem to get better, but my buddy has an 09 and I have a 2011 and they are both incredible.
_________________ John 2011 A22
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