crashz,
Some have some good advise here and some seem a little bitter. I do exactly what you are talking about with a 4x4 JD 4320 48/40hp with FEL and a mx6 cutter. This is not done to put food on the table, but rather to make enough to pay my note, have some attachments and help with my tax situation. Besides, I enjoy the seat time. It would be very difficult to depend on this to make a living. This is my take on the situation:
1. Definitely buy liability insurance. Failure to do so in today's environment is completely ridiculous...and dumb.
2. You WILL find the occasional piece of property that has partially burried chunks of concrete, rebar, steel, fence posts, rolls of barbed wire, or the engine block the property owner forgot was there. Oh yeah, don't forget about the holes that your entire front end can fall into... Therefore, you must have medium to heavy duty equipment if you expect it to last. You will be disappointed if you try to get by with cheap equipment (been there, done that). Further, you MUST be prepared to deal with some repairs, no matter how good your equipment is. Keeping this in mind, sometimes, you have to pass on some jobs. They just aren't worth the risk.
3. I keep it small. Most of my work is brush cutting property less than 5 acres. I look for small pieces of commercial property that have to abide by the city landscape ordinance and keep their property within reasonable standards. I look for property/conditions that the local landscaping companies either don't have the tractor equipment to deal with or don't want to bother with. Conversly, I look for property too small for the large equipment operators to bother with. I realize this is a small niche, and therefore, I am not swamped with work....but I don't want to be... I have a "regular" job and a family.
4. I don't try to compete with the lowballers or those who don't follow the law. If you want me to maintain your property, you are gonna have to pay. I evaluate the property and give a total price for the work the owner wants performed. My minimum is $100. I don't care if you want me to bush hog 1/4 acre. I will not show up for less than $100. My goal, when determining a price, is to figure $100 for the 1st hour/acre and $65 for every acre/hour after that. I'm not gonna waste my time for $40 (about $10 profit) per hour when I have to pay for fuel, maintenance, insurance, taxes, etc. I have a "real" job that takes care of my families primary needs.
5. I follow the laws of the state of Mississippi and actually pay taxes on all my income!! I know this may be a little unusual, but I feel it is the right thing to do. However, there are some substantial tax benefits for MY situation. So far, for the last 3 years, when counting all expenses and depreciation, this part-time tractor business has had a fairly significant positive impact on my overall tax situation.
If any of this makes since to you, and you are selective as I am, you may find this type of work enjoyable. However, please beware and considerate of the many pitfalls that can take something enjoyable and turn it into a nightmare.