yea, I would call every 500 miles extremely diligent. Thing is though, make sure you are getting your standard chain really CLEAN before lubing it...best process I have found for standard chain is soak in solvent of choice (gasoline, kerosene, diesel fuel, old carb dip, whatever), scrub, rinse,dry it out, grease with high temp bearing grease, roast the grease with propane torch so that it melts into the pins and rollers, wipe off excess and its ready to go...but personally, I can't do this every 500 miles, so I use o/x ring chain...
to get a 750 to do wheelies with just a sprocket swap you will have to run some crazy custom sprockets and you will barely be able to go 70 mph, plus a 750 is still a big heavy monster with all the weight up high and to the front. I like 16/17 tooth front 48 rear for the acceleration, but you still gotta dump the clutch in first at about 7500 rpm to get the front wheel off the ground just a little bit with a stock/lightly hopped up motor. If you really want to do wheelies, I recommend Buell XB9/12. They are pretty cheap right now, and you will have trouble NOT doing wheelies.