From what I gathered from your posts, OP, indicate you are not in a position to do this right now. You are fretting over the costs of insurance. You have a bunch of homeowner equipment, most of which is wore out. You have a trailer that you dont trust, have little or no money in the bank, and have very little time and income. You may have a passion for the work and the drive to have a successful business, but it will take more than that with a family and full time schooling. I strongly recommend you get a job and start saving some money. You need to put money in, a lot actually, before you can think about pulling money out. I am a fan of using credit to start a business, and have recommend it to some others for a variety of reasons. However, I can't recommend it for you, as you have no way to make the payments. I took almost 10k in a loan for all the equipment I needed just to get started, had 15 weekly customers and after it was all said and done, I took no money out of the business. It paid for its self, and bought more tools, and made its payments through the winter, including the note on the equipment, the note on my truck, and insurance through the winter. It didn't pay for the power bill, water or gas, The mortgage, wifes car payment, student loans, food, or fun. That was all paid for through my other job. With this in mind, I strongly urge you to consider working and building up some capital before you dive into this, even if that means go mowing for another company while you learn the ins and outs of the business. I jumped into this business without any other experience in it. It cost me money as I lost some while part of the learning curve. I was ok with this, I knew it was gonna happen, but I was ok with it. I'm a do'er. I dive into things and work them out. The difference is, I have another job at $27/hr that gives me some of the best benefits in the tristate area that was there to float the business while I learned. Not everyone can do this, so not everyone should do it this way. Especially if you need to support a family at the same time. Don't act on emotion, act with a clear business mind and move accordingly. Emotion has no place in a business. As for your initial questions about insurance, the hard truth is your 19. Insurance is expensive under 25, no matter what the type. Statistically, you are more likely to have a claim than I am at 32. I may not be safer, but statistics show you are the higher risk. So for this, you will pay more. I would recommend you get a 1 million/2 million General Liability policy. It is pretty much standard. It will cover you for a broken window, or burning a house down from a brush fire your hot muffler started. As was stated, if you cause major damage and someone wins a suit against you, it will follow you into perpetuity (meaning forever, until paid). The insurance will pay the claim, instead of your wages being garnished forever. Also, you may want to call your auto insurance company. Make sure your sitting down, then tell them that you are going to be using your vehicle for commercial purposes in lawn care. If you thought GL was expensive insurance, wait till you get your premium on commercial auto, then add a plow rider to it...oh boy... My first year, I paid just over 2000 for the year for commercial auto, general liability, inland marine coverage. (Inland marine coverage covers your equipment if it is lost/stolen/damaged/etc). This year, I am gonna pay half of that going with Erie.