Well now the guy's in his first year and for that, 250-300/day is pretty good. To be blunt, that's kickin' azz.
Far as the ceiling, it takes T-I-M-E so don't worry about it and just keep doing what you're doing and one day the ceiling will magically have disappeared but you can't think about it too much, just keep working, lalala...
Most I've ever grossed is 500+ but what some folks fail to tell you is that was AFTER 150 in expenses, so suddenly it's not so impressive anymore. For me, I did 200 dollars in 7 hours today and I'm cool with that, dunno for sure whom to believe around here when it comes to this but I believe you speak the truth. This isn't the busiest time of year, thou demand is high, the days are short and I can't get the hours in regardless, 40-degree temps slow me down hard in the mornings...
Come spring time, I can do 300-400/day, but that's 6am until dark and that's JUST grass-cutting. If I do some of the other stuff (like mulch), I can do 500+ but again, it's AFTER 150 in cost of mulch alone. Well schitt any idiot can quote 150 for cost and 50 to drive to the mulch yard and load up for the 200 and spend money and talk about they made 100 dollars/hour but they didn't really earn but 25/hour after they paid for the mulch now, did they?
pssshhhhh....