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Going to a 96" means a complete engine teardown and a new crank - your crank is 4 inch stroke and a 96 or 103 is a 4 3/8 inch stroke. New crank equals probably about $2000 more of your money all else being equal. I would go to 95 inches which is a big bore or maybe 97 inches (Max big bore) 10 to 1 compression max. While you are in the cam chest freshening stuff up you might think about the upgrade to the latest style cam chains and oil pump and cam plate. One thing leads to another and you could easily drop some serious coin on all the stuff you mentioned. Maybe out there is some guy that has an 11 or 12 or 13 ultra that has to have the water cooling, fairing upgrades, yada yada. You might be able to trade for nearly new not much more?
Just my two cents.
Actually ya can bore an 88 to 95, 96, 97 and even 98. Going bigger would mean splitting the cases for overbore and/or stroker crank. Ya could keep the 510s for a mild build but if ya are going bigger, go bigger. It doesn't cost any/much more. With only 43k i wouldn't worry much about oil pump/starter/stator unless there is a problem. They can be checked if ya do a rebuild.
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