I would take a walk around your yard with a tape measure, and measure distances and clearances for the mower size you are considering, are the trees all mature? I have found over the years that what I could fit through at one time, I can't anymore, I am basically limited to a smaller deck size than I would like, but hey, what is another lap or two....
I would also have a heart to heart with your dealer as to whether a Mid mount or a 3 pt finishing mower would fit your needs.
I'm thinking the ease of hooking up and unhooking a 3 pt would be easier as well it can also be used as ballast when using your loader, providing you have the room for it out back and it doesn't get in the way of loader work as it adds a lot of wheel base.
I had a mid mount machine once, and went to a zero turn, but for the bigger jobs I bring out the big guns, the 7060 with the 80" flail.
I would consider a pirhana bar for the bucket, it will save the factory cutting edge, add rigidity to the bucket and they are great for scraping ice off of all that blacktop.
Most of all.. have FUN!
Cheers
Roger