ValleyDweller,
I will jump in here as well. For cred, here is our website
* Hanna Bechard * A Woman's Touch * Clarksville * TN * Landscaping * Lawncare * Patios * Ponds * and we have been in business since 92 or so. (and actually a bit before that in some respects)
I have a full time job, with insurance and all the bells and whistles (as you do as well) and the wife does the lawncare business.
What you are looking at doing is entirely reasonable. Many folks do it, and succeede, although many also fail. IMO you are doing it right by evaluating it before jumping in. It looks to me like you are taking the high road by being "legal" but most folks do not start that way, and they slide into being legal as the business develops and they learn more and more about what "legal" is.
My advice I would give you would be
1. Find a good small business CPA. Not some firm with lots of letters and names on the door, a guy like yourself, that holds a CPA and manages the books for other small firms. Ask others in similar small business's how they do it. This person is our most valued outside asset in our business.
2. Try not to buy the next "tool" thing, widget whatever that will make you a bunch of money. Try and work with what you have. (I am miserable at this)
3. Think long and hard about the LLC thing. While you will have many folks tell you (and I think I saw it in this thread) it will "protect you from being sued" etc. etc. or "protect your assets" take that advice with a grain of salt. You launch a mower blade through a window, the business will be sued, you will be sued, the mower manufacturer will be sued, the blade manufacturer will be sued ad infenum ad nauseum. There is a lot more then show on the surface to being an LLC and you still are out there on the line. We operate as a DBA, and constantly weigh out the benefits of going LLC.
4. Find the "right" insurance agent. Long story, but the "right" one will look out for you, and get you enough insurance without running you bankrupt. It is easy to talk yourself into an insurance hole. I just learned a month or so ago that I did not have liability insurance on the trailers behind my business trucks. My "previous" agent said, "well, do you ever tow a trailer in your business?" I about fell over.
5. Don't lowball. Easier said then done, and we get lowballed every day. Recognize that the guys bidding that price that you think you can do for half, many of them have done it for a while, and know what the costs will be and are trying to make a living. If you want to be in it for the longhaul, then plan on being in that line with pricing.
6. Don't work for nothing, or too lose money. There comes a time where you start dropping your price to where you have work, or get the job with the anticipation or promise that more work will come. (that seldom if ever works out) One of my mentors Chuck Shoope said too me, at the end of the day, you can go to bed broke and hungry or tired and broke and hungry. No need to be tired if you did not fix the broke or hungry problem.
7. The secret to making it in small business is too only work half days. The good part is, it does not matter which 12 hours you pick
The last of this long winded thing has to do with pricing.
We do not price things by the hour, or the acre, or the whatever, we price by the job.
There are two schools of thought from my standpoint. Lets call the first the "time motion study plan" or "detailed analysis" plan. That is the group that figures everything out, in mowing they walk the lawn with a measuring wheel and calculate running feet of trim time, they figure the square footage of lawn area, they figure travel distances etc. etc. there are computer programs and charts and graphs with circles and arrows on the back to be used as evidence against us
Then there is the us, which is actually more common then you would think reading bulletin boards etc. Which is, every yard etc. is different, and every job is different, you go out and look at each one, stare at it a while, and get a feel for what is going to be involved, and what the hassel factors are, you weigh it all out in your mind and shoot them a price. That is what we do. Sometimes we are high, sometimes low, but all in all, with the years of experience we hit pretty well.
Good luck, wish you the best, build partnerships carefully, work closely with your support folks, it can be a great deal.