Rob,
I'm mowing with approx a 16' gang and i love it. Bought it from a friend who use to own a golf coarse. The mower i have is a steel wheel ground driven Jabacson rough finish gang mower. It is a totally different way to mow, your grass has to get conditioned because you are cutting it instead of beating it with a rotary blade. My gang mower has cut my mowing time by about 60 percent but. . . . gang mowers don't do well with deep grass, you need to keep on top of this to mow effectively, i mow very tight and mow now about every 2 weeks. I got my gang mower late in the season this year so i'm not mowing all 33 acres because it got away from me this year but next year i expect to mow all in about 5 hours. The faster you go the better they mow. As for sharpening my friend told me probably every 2 years on the sharpening and he'd do it for free.
These mowers pull quite hard and i guess the set i have weigh in about 1500 - 1600 pounds, at first i wanted to go about
24' wide but my land is kinda rough and hilly, i found 16' is a nice cut. Each one of my mowers are leaf spring suspended so they run smooth and hug the ground while riding on steel wheels which eliminates the need for tire replacement and work better on wet ground because of the wheel design. As for a brand my friend Ned says stay with Jabobson or Toro because of parts availabity and they have a good track record for reliability. Sorry i have no pictures cause my camera has turned up missing . . . .Also they are not cheap to buy unless you have a connection but in my opinion are well worth it if your mowing any amount of acreage . . .Good luck, John