Q: Should I be the one to hire the gardener/pool cleaner? Or can I let the tenants do that?
A: YES YES and YES. The tenant will NEVER do any yard work or maintenance. You can easily hire a weekly gardener for under $100 to come by to cut the grass, spray the weeds, etc. For pools it's about $150 once a week. Unless you want dead overgrown jungle grass and a pool of green algae, always contract out the work. You will be 1) preserving your investment and 2)keeping your tenants and neighbors happy.
The last time I didn't hire the work I had a weed jungle and a pool that became a habitat for stray turtles. Don't be cheap, build it into the rent if you want. But do not neglect maintenance.
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