Plan on double cutting every lawn with a Craftsman Zero-Turn mower. Invest in a nice Walk-behind for a couple thousand dollars. All suppliers have some sort of financing.
You can use whatever push mower you want because you should only use a push mower(22" or smaller) when you can't get through a gate.
Otherwise, you should be using a 36" walk behind mower. You can get a 36" World Lawn mower for $2000 and a Toro/Exmark for $3000-$3500.
Look for a used 5x10 trailer on craigslist or eBay.
Invest a COMMERCIAL weedwacker and a cheap backpack blower. A Husqvarna 130BT is a $200 Backpack blower at Lowe's. All of my other equipment is Echo.
There is an Old Blue Chair for each and every one of us, we just have to find it.
2006 GMC Sierra 2500hd crew cab
BOSS 8'2" Power V
Hustler X-one 60"
Toro Proline 36" wb w/t-bar controls
JS46 22" walk-behind (wouldn't recommend)
Shindaiwa T254, Echo trimmers, chainsaws, pole hedge trimmer, pole saw, hedge trimmer
Shindaiwa 633 and Husqvarna 130BT blower