The biggest hurdle i think is the tipping point, There will come a time when your picking up more and more work, and you hit the tipping point, this is where you need to make a choice, either you stay small/solo, or you crest the hill and have start hiring people. The problem here is you NEED to keep growing once you crest the hill and hire someone. You have to start crunching the numbers and see just how much you need to grow with each person you hire. For instance, if you hire someone for 12-13 bucks an hour, he will be pulling $500-600 per week, So now you need to grow your business to support paying an extra $500-600 per week. So if your mowing $50 dollar lawns you need to pick up 10 more lawns just to cover the cost of your helper for the week. But whats the point of just picking up an extra 10 lawns to cover his pay???? Now you need to pick up 20 lawns just it make it worth your while. Now you need to start buying more equipment, your using more gas, more wear on machines etc etc. You need to be smart and know your numbers, or else you will actually be making less money at the end of the day with helpers and 3X the work you had before as a solo op. On the outside you will look like a bigger company but on the inside you will be making less money then you did when you were solo and had half the headaches.