Hey mate, Welcome aboard!
I will try and go through your list for you.
First of all you have mentioned how you will like to fish a few kms outside - I wouldn't consider a bowrider then which is the cruiseAbout. At first it looks very appealing, lounging at the front etc and it is the same thought I had when I first began. When you go offshore you want a high cockpit to take on the waves, yes you can do it on a bowrider but you wouldn't enjoy it as much. You will feel better being higher up.
a 5M + cabin boat is what I think you need. Yes it is still a champagne boat! You definitely want over 5m if you want a bit of room and you will be fine towing it too. With the cabin boat you will have bunks to rest, hide from the sun and drink champagne while lying down
These boats can come with a ski pole so not a problem there. Not sure about the dining table (if that is what you meant) as an option, but they can be done after market if not.
Now the motor! If you like speed, power then you are like me... you will like 2stroke. 2S motor's these days are oil injected, more torque, lighter that a 4S, cheaper to service. 4S are great too, great fuel economy, quite but you won't have the hole shot performance of the 2S. These days either way you are fine, just comes down to what you like, what your dealer offers. Depends on the boat you get, you will get a range of HP to put on the back, I always go for maximum power but don't forget to consider the balance of the boat, a lot forget that and then have a bum heavy boat. Try and find a good balance.
Stacer make a good range of boats, look into the Sea Runner.
I know what you mean about the boats condition when they are new. They been sitting there for ages in the sun, rain etc so they get dirty. Too many boat too clean!
I would prefer to get it wrapper or leave it white. Have a look at the boats with coloured hulls that have had some minor accidents/scratches. Makes it easier to stand out.