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I used a 21" mower my first season. I bought a 36" walk behind next.
I chose that because most of my lawns were "smallish" in size (remember, I was initially bidding on lawns I could mow with a 21"), and I had several with gates to back yards.
It's faster than the 21", but if I had lawns that were more level and "square", open spaces, I'd have gotten a bigger deck.
You need to get something that will get through a standart gate-less then 30 inches overall width, the 36 inch would be good. its small enough to get into back hards, big enough to quickly cut yard. IF you get bigger yards then get a bigger mower. I started with a 34 in ZTR, used it for two years, then supllemented that with a 50 inch ztr, as this year i got several 1 and 2 acre yards, Had two 1 acre yards from the begining, and now i just fly through them ( 30 minutes instead of 1.25 hours)