You'll most definitely need to spend a lot more than $250 on advertising to get a decent core of customers. And like somebody mentioned earlier, you don't need a trailer right away. If you'll be doing a lot of small yards, your gonna spend almost as much time trimming, edging and blowing as you will mowing. So make sure you get good commercial stuff. My first year solo, I did about 40 lawns a week on average, with a 21" John Deere (had to buy a 2nd mower halfway thru the year, it was a good mower, but not designed for commercial cutting) and Shindaiwa trimmer and edger. Also a little Stihl handheld blower. Still going solo my 3rd season, have about 70 accounts total, mow about 60 or so any given week now (5 days, plus a little bit on Sat.) So I also have a little time for extra non-mowing jobs as well.