Ok, here you are, You like lawn care and want to possibly do it when you retire. That is exactly what I have wanted to do for so long. I worked so hard at my full-time job and they kept taking away the benefits that made working their worth while. So when my son got type1 diabetes it put our backs against the wall financially. So I started my part-time lawn care. 40hrs. per week plus another 30-32 doing my lawns. For three seasons I killed my self 20-22 lawns a week. Even 6 lawns could tie a person down. Get the picture? If I did not desperately need the money I would have waited till just before I was going to retire before I would commit to doing this on the side. The work will always be out there if you do good work, I would work with you friend to make sure if that is what you want to do with out putting out for all the equipment, Insurance and so on. By the way I am now retired from the other job and this is the first season in four years that I actually have the energy to play some b-ball with my son after working. You don't get the time with you spouse, son or daughter back when you over extend yourself.