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I would suggest against the maintenance world- unless you have a dedicated trustworthy employee who can take care of it for you. And if he she is too good they will try to steal it from you eventually. I tried maintenance for 3 years thinking exacly along your lines, but it was one big unprofitable hassle. How may complaint phone calls are you willing to field regarding clippings in beds, or long grass after a week of rain? Who will take care of the route when the main guy quits or gets sick? Who will drop everything and drive across town to show the main guy how to put new line in the trimmer for the 15th time? Who will apologize to clients after someone mows over prized petunias? Who will spend 8-10 hours a week billing (or chasing) clients who owe $90? Who will finish out the season when the main guy quits on October 15th? I had to answer all of these questions and a hundred more just like them repeatedly in my three long years of maintenance. I dumped it last year, and boy am I glad.