Canada has a program where you can import a child-care worker on a special visa. I know this because I saw a program on how it was being abused on Canadian television. Theoretically, they are supposed to get days off, etc.; some people take advantage of the threat of visa reovcation to nake them work slave hours, skip wages, take away their passports, do all the housekeeping, even pass them on to their friends and physical abuse. Good old first world. However, the recruiting agecies back home apparently also get in on the exploitation action. The leverage in the arrangement is very one-sided.
Apparently, you can get a full-time, live in nanny for your child-care. The number mentioned was about $1000/month. Currently, a lot seem to come from south-east Asia, especially the Phillipines. A few decades ago, the nanny of choice came from Jamiaca; since the visa was a help to full immigrant status, this is where a lot of the Jamaicans in Toronto got their immigration papers from.
A well-off couple who do not qualify for subsized day care could conceivably spend over $1000/month on just day care, especially with more than 1 kid. This option is a real bargain if you have the house with room for a live-in nanny.
As for anything more than that, per the OP? You need a gardener, there are landscaping companies that contract for that; they take care of finding people, maintaining all the equipment, on grass-cutting day 10 people show up and the whole 10 acres are trimmed in an hour. A guy with a front end loader shows up after the snowstorm and your driveway is clear in 10 minutes, Ditto for house-cleaning. Instead of one person who lives in, enough people show up to finish the work in an hour or two; someone’s vacation? They worry about filling in the gap. Don’t like the result? The owner of the company sorts out your complaints, and Consuela is replaced by someone else and never shows up again. For the pool, a trained pool-boy will adjust your settings so the pool stays clean and clear.
Chauffeur? The company I used to work for, apparently the high mucky-mucks in head office had drivers (along with a private dining room on the 24th floor in an office tower). Rather than fighting through a 1-hou city commute crawl, they sat in the back and read reports and the driver dropped them off in front of the office, took care of parking, and picked them up again at 5. Convenience is a perk. But, evenings and weekends, unless it was company business I assume they were on their own. The chauffeur did not live with then and enjoy the perk of banging the upstairs maid and the lonely missus.
The only guy I know who did have a servant (a live-in nanny when the kids were young) was an eccentric type who among other things, stayed fit by doing his own gardening pusing a lawnmower around an few acres and raking the leaves every fall. He also fixed up a lot of his run-down turn of the centurn mansion by himself. Some city workers once stoppped by and asked him who owned the place. He said he did. “No you don’t,” hey said. “We’ve seen you here. You’re just the gardener.”
It’s so much simpler to have contractors today, and so much simpler if you have your own private house and don’t have to run a household for a few extra live-ins. You don’t have to try and find a jack-of-all-trades to do all the different tasks a modern household needs. Not too many people can afford enough servants to hire one for each task. Plus, wages and labour standards today make it difficult to demand the round-the-clock service we associate with old-style servants. Those standards are a by-product of the abuse the old-style rich people did heeap on their hirelings.