I pay a lawn service for my rental property because its 4 hours away. I hate it so so so much. The property is a duplex though, and the last thing I want is a squabble between the tenants over mowing, so I provide it with the lease.
I've been through a few landscapers and while the guy I've got now is the best one I've had, they never do as good of a job as I would, and the intervals that they come never seem to be right. In North Carolina, you need to mow just about every week in the spring and early fall because the weeds will take over and kill your grass if you let it get too long. But in the summer, the grass grows slower so you don't need them to come every week, but they sure don't mind coming and charging your ass for it. And in the fall, the leaves all seem to drop at once in North Carolina, and its usually right AFTER the lawn service people have come so they sit on the lawn for a week and kill the grass that they've been abusing all spring summer and early fall. They also never do a good enough job with the shrubs and beds, they nearly always look messy so I drive down a couple times a year to do a full bed cleanup. It'd be great if they'd do it though.
All that and it still costs $250/month, which is apparently a bargain after talking to some neighbors. Landscaping the only thing that I haven't really been able to get right on my rental after almost 5 years of renting it out.
So anyways, facepunch time. Unless you have a physical disability that precludes you from mowing your own damn lawn, you should be mowing your own damn lawn. And even if you have a physical disability that precludes you from mowing your lawn, you should reconsider your living situation rather than paying someone to do it. If you have enough money to be considering paying for landscaping, you should be giving more to charity.
As far as the HOA stuff goes with respect to the south vs the north, I sortof get it. If you don't keep up with a lawn in the south, it quickly turns into a jungle. My neighbor at my rental property used to rent to a tenant that never mowed, and there were bushes 6 feet high in the backyard when he moved out. The landlord had to pay a fortune to have it cut back, and the thing that annoyed me was that the mosquitos from that un-maintained brush were absolutely terrible in my backyard. I don't have an HOA, but it would've been nice to force that guy to cut his lawn.