First motorcycle- looking for a reliable cruiser for commuting?

[Thud]

I want to spend 2-4k on a used bike that I can learn on. I'm considering the Yamaha V series, the Honda Shadow, and the Suzuki Boulevard. I want something that is reliable and has a more classic/retro look.

Initially, I thought I was sold on the V series because I was finding 4 or 5 yr. old bikes for under 3k. But after a little more research, found they are air-cooled, and (some claim) are not intended or uncomfortable on long rides. I'm 6'2" and 230 lbs, and don't want to look like "Shaq riding a pony" as someone put it.

I also read that the V series requires a lot of maintenance. Does the inconvenience/cost of this maintenance negate the benefit of the V series' low cost when compared to the Honda and others?

Gas mileage is also a concern b/c I intend to use it as my commuter... so I'll be riding 30 min to school, 30 min to work, then 30 minutes back home almost every day.

Any advice would be appreciated.