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I don't know enough about sole proprietorship vs limited liability, but as far as the amount of time it takes to mow, it takes me 4.5-5 hours to mow my 11 residential lawns. None are larger than 1/4 acre. 3 clients are next door neighbors to one another so I knock them out in under an hour. If you only have a couple days a week to do it (like me) I would consider the chance of bad weather before picking up too many more than 15, maybe 20. Not every day is a good day to mow! Best of luck, you sound pretty busy.
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