Seriously man don't do it!
There are probably plenty of Insurance companies you could work for that would fit your goals. You're going to be scrapping over Florida cheap lawns. Not sure if you did the health insurance side of the Business. Really will be a struggle to get affordable health insurance. At 29, you really need to think about that. 50 comes around pretty fast. Now if you have saved a lot of money and have investments... But you say you are buying used equipment....
So you have 11 more high energy years. Start dropping off in your 40s. Can get much worse in your 50s. The Florida heat and humidity won't help any. 30 average Florida lawns is a drop in the bucket from what NET income is needed to get out of poverty for your area.
Some say why be so negative. People going into any business sometimes ignore reality. Ignore the negative aspects. Oh I am so unhappy, I just need a change! Read this forum. Read the good and the bad and the ugly.
How to get business? I would hate to be a newbie in already saturated lawn care. Like has been said, post cards are one good tool. Family, friends and neighbors. One lawn sometimes leads to others. That is if you do a great job. You will do a lot more driving than working at first. I would not resort to low balling your way in. You can't go much lower in Florida anyway. In 5 or 10 years you will have to replace everything
Seriously man, don't do it!
Wow, seriously why bother being part of lawnsite if your just going to bash someone attempting of starting their own lawn business.
Advertise on the side of your truck or trailer. Drive around and ask people you see around areas you want to work. Drive around on weekends and late afternoons when people are home. Be seen and people will think you must be doing good cause your "working" all over the place. Dont really need to be seen working just in the area.
I dont advertise but I always waive to neighbors or any one looking my way. Sometimes people are scared to ask and a simple waive breaks the ice.
Dont get desperate, summer is coming and last year I had plenty of new customers needing service. This was in established areas. Most new construction over in st cloud ( south of orlando) 275 to 300k for house and people dont have the money for a basic 80 a month lawn service. I still try to get into subdivision close by (new) but most people dont have the money or get it for 60. I'm in it to try and make money not a charity.