The state you live in dictates taxes etc....dont cheat the man, getting bit will haunt you for life.
Find a good insurance agent, someone who wont pawn you to a minion, make sure they listen. Then work with them to figure out what you need for coverage....dont forget injury, disability and workmans comp if you have employees......dont pay under the table, if someone gets hurt its a nightmare.
As far as equipment.....dont buy crap, i still buy quality used stuff. Find a good repair shop and buy what they sell, this way parts are all most always on hand and you are back up in no time. You can buy 5 used walk behinds of good quality for the cost of one ok z turn new. A big mistake many make is financing a butt load of brand new equipment and having to few customers to pay for the gear.....dont work for your equipment, it works for you....my repair shop sells toro and echo .......toro owns exmark so he always has what i need and knows my equipment.....dropping off a case of beer every now and then always is appreciated as well. Get some good hand tools and learn to do the small repairs on your own. Do your preventative maintanence.......keep stuff clean. Change your air filters and oil when you are supposed to. Go easy on your hydros, those pumps are expensive repairs
As far as upgrades...im a huge exmark fan....they have done me very well, they hold up to good care and to abusive workers. A good walk behind can be had used for 1000-2000 bucks, a good used z turn 4-5000...exmark numbers. Buy what you will use the most, if you only use a z turn for one yard....why bother, i use a push on two properties for 5 minutes each, hence my hunk of junk. Watch your spending on equipment.....and know that you will have repairs. The bigger the machine the bigger the repair cost. Also make sure the machine you buy has an engine fit for commercial duty.......a 72 inch z turn is no good with a 17 horse briggs replacement.
Your equipment will do more in a week than the average homeowner will do in a year....i like stuff with big motors, they dont strain to get through the day, think about a 4 cyl engine in a sedan vs. a 6 cyl......the 4 uses less gas but works 50 percent harder to do the same job....adding 50 percent more wear and tear
Last but not least, go slow, do what you can handle......its a lawn, nobody is gonna die if it isnt green enough. Be nice, dont take abuse, not everyone can be made happy.
Exmark Z 60" w/ ultravac
Exmark Z 60"
Exmark Z 56" triton W/ ultra vac
4 echo Pas 266 with 2 of everything
3 echo srm 230 whackers
Echo 330t 12" 341t 12", 400 18", 440 16", 550 20", 6000 36". Husky unknown frankenstein 32" that could chip the terminator!
Echo PPT 280
3 echo pb 770t
2 echo pb 755t
4 echo hc 165
2 echo hc 185
And...... 1 1980s snapper hi vac i found in a trash heap that only needed a spark plug.....still running strong with a little duct tape and silly putty!