Here are my thoughts now that the game has been changed. Here is what I would buy if I was starting out again with that much money. I have found that I am always in need of 3 types of mowers, a 32inch, a 52inch, and a 72inch. If you have a narrow 36inch gate how are you going to fit a 36inch mower that is actually 37 and change? Next are your normal suburban lawns about 1/2-1 acre and now all the walk-behinds are to slow so now a 52inch is perfect and its not to wide if you have a bagger on it. Now when you get those big accounts that 52 wont do it efficiently so thats where the 72 fits in. I would even get a diesel where you can because your fuel bill will go down dramatically and against popular opinion of those who don't own one its way cheaper to maintain. Here are what I think are perfect all around machines to start with and id get 52inch in all of these http://www.ferrisindustries.com/us/e...ers/evolution/
(dont go smaller than a iz2000), http://www.scag.com/vride.html
, or http://www.scag.com/cheetah48-52.html
Now if you can handle it I would not go smaller than a 18ft trailer for your first one. My 18ft is sooooooo handy when I have to bag grass, leaves, remove trees, haul lots of prunings. If you had a 10 or 12 ft there is no way you could do the big job efficiently. Then if you have to haul mulch, rent min skidsteers + haul dirt and so on. I've hauled 3 yrd of dirt plus a dingo on a trailer before. Its so handy.