My two cents are that I am glad I started on a small bike and worked up. Went from a 125 to a 350, then to a 650, then 1100, now 1200. Learned to ride a bit in the dirt.
However, despite that experience, I dumped 2 of 3 dirt bikes and dumped both the 650 and 1100 on the street. Wasn't doing anything stupid on any of the bikes, but each accident got me anyway. Dirt bikes just tipped over, really, in the dirt. No worries. But I dumped the 650 on a wet road doing about 35. Luckily I had full riding gear that day and didn't even get a scratch. The bike nearly smacked a parked car, and it was lucky that there was no oncoming traffic. Dumped the XS1100 because I got a speed wobble / tank slapper / head shake in the middle of a turn. Was able to straighten up and ride it out until I hit some grass at about 15mph and dumped it.
Nobody likes to talk about accidents, but I have ridden probably 50 different bikes and have decent riding experience. And the accidents still found me.
If you're like me, you find you quickly want more from a bike, but a healthy amount of time on the right starter bike does not hurt.
I would not recommend a 250 for you unless you are very small or have balance problems, but I wouldn't recommend a VMax for you either, due to it's pig heavy weight and power. When you wake up the bike and find out it's fun, trust me, it's hard to ride like grandpa, so I have to wonder about you saying you won't push the limits on a Max. After all, the Max was built for one thing, and I don't know anyone who buys a Max and isn't tempted to see what VBoost is all about....
The XS11 is just as pig heavy, but I am to a point now where I can turn it all the way to the stoppers and do 5mph turns, stops, figure eights, etc. I know the braking limits, speed limits, and I definitely know about speed wobbles. The bike finally "feels" great.
If the Max feels great to you, go for it. If it doesn't, take the safety course, respect the bike, learn to countersteer, and ride like you are invisible. Go nice and easy until it does.
I think most motorcycle riders will experience an accident at some point. Hopefully you won't. But if you do, hopefully you can come through it and learn the lessons. Because sometimes you just can't predict when the tire on that 5'th wheel camper up ahead of you is going to fly off the axle at 85mph, swing across your lane and almost take you out.... or that chick on the cell phone who runs the stop sign..... or that sand spill in your lane up ahead in front of some vehicles that you can't see... or....
You get the idea. Just be very careful.