Here are my final thoughts now that we know you have some money:
Trailer: 5x10 up to a 6.5x12 $1200-$1500
36" Walk behind: World Lawn $2,200
Toro/Exmark/Scag, etc. $3,400
I really like my Toro Proline t-bar 36"
without a sulky
Weedwacker: Echo 230 or 266 $300
(Im an Echo guy)
Backback blower: Echo 265 or 500 $270-320
The range would be $4000-$5500,
plus $500 worth of shovels, rakes wheelbarrows, maybe a hedge trimmer( I have the Echo 150, now its the 152. It works great for me and I did 4 major landscape clean-ups were trimming was needed, and used it around 40-50 times for regular trimming.)
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