There is lots of advice in this thread, most of it good, IMO. Go back and read TurfTurf -- the posts are simple, straight-forward, easy to understand. Also, the advice to work with small business counselors. As somebody said earlier in a meeting, lots of good advice in 90 minutes. Some places offer day-long seminars that cover all aspects. Getting hung up on the costs of insurance at this stage is to be in the trees and miss the forest. Yes, it is important and necessary (should be $1M for liability, $2M is only a little more expensive), plus property damage. But, the business plan here is critical. Oh yes, financial management software is a necessary component. Quickbooks works for many on LS, and is only about $150. As for scheduling, with your small operation, 3X5 index cards are all that is necessary. Punch a hole in the corner, put them on a ring, and continue to insert them into a new location after every property visit. The ring insures nobody gets lost, and is continuious. Inexpensive, works well, and is easy to understand. If finding a job in your area is so difficult, what is the potential for finding lawn service customers? Is the profile of potential customers include those who consider hiring lawn services absolutely necessity (e.g. elderly who cannot do it for themselves), or discretionary (work that can be done by a homeowner, but chooses to hire it out)? If the employment pictures is so dim, perhaps the pool of potential customers is also very small. What I am asking, "Is there a market for your services?" Family is one thing, but finding independent folk needing your services is something else. If the market isn't there, then your entire plan may be a moot point. Remember the demise of most start up businesses -- undercapitalization. From what we've read here, you may be in that pool. To the OP, I really appreciate your courage to lay yourself out here, and willing to dialogue. And, as somebody else said, your tenacity. Good!!! Perhaps others considering starting a business will read this, and start to understand that starting a business isn't so easy. This thread lays out many of the obstacles that are in the path, many of which are unrelated to the insurance question. In the big scheme, a start-up in lawn services is one of the easiest -- relatively low cost (yes, much as been said about capital, or lack thereof), no particular training or skills. So, it is attractive to many. For more specialized business startups, the obstacles are much more complex. I mentioned day-long seminars about setting up a new business. Go to one of these seminars, and you will quickly understand the simplicity of lawn services.