When I lived in a townhouse just out of college I mowed the grass with a push mower. Quick and easy.
When I had an acre in my 20s I paid someone $60 for each mow and blow. Being self-employed and motivated I could make more than $60 for the time it would take me to do it, not to mention the tractor maintenance.
Now in my 30s, with kids and about 1.5 acres in FL where things grow year round, I pay $260 a month for full service and it's worth it. A full crew does the mowing, blowing, weeding, bush trimming, spraying, dead palm frond removal and I can either be working or around the pool with the kids.
I've had discussions about this with other guys who scoff and say "oh you can do that because you have money to do that" but yet they are usually the ones with new cars, new technology gadgets, cable TV, etc. which I have none of. Some people just value money and time differently. Though I'm still a lucky guy.