I'm a tremendous judge of character.
If you give a hoot on my opinion of how you will do with the Tennis Club set, let me see you talk...
If you want to be a successful Owner Operator in the truest sense of the word, you have to set your sites on rich middle aged ladies who put a huge value on how trustworthy and likable you are. Your cleaning equipment, skills and outcome play a distant 3rd and 4th. If and when you start landing these sort of clients you MUST make it your goal to get in with her friends.
It won't be a cake walk because one, she'll fear that sharing you will lead to her not getting her appointments easily set because you'll be too busy and two, you may be dealing with a house manager most of the time who can't afford you personally so she won't be spreading the word, BUT she may tell other house managers if you are easy to work with and make her life easy.
Your goal should be to shoot for a $400 plus job average. Can you do ok with a 250 average? sure but this shit is too hard for just an OK income. Easier to just get or keep your current job. The Entrepreneur dream is to make bank not bucks
How do you get to a $400 plus job average? Clean lots of tile and stone, expensive furniture and rugs in the home. Unless you aim to hire and buy buildings, forget the rug fag dream, you'll be up all night and working weekends washing rugs for $4.00 a foot when you could have gotten $2.00 to knock em out in the home. It's the newage rug reality.
Don't try and get your average up by selling deodorizer and protector services with customers who you want to service over and over again. That bullshit is for once and done advertiser driven customers.
Take the Stone Pro class, Take Jim's fine fabric class, come to Mikey's Feest in November
Keep your overhead low, answer all your calls asap in the beginning (they'll wait for a return call the next time) and run out of your house if at all possible. Stash and invest cash like crazy as your "Business" will be virtually worthless when you call it quits.
Don't get injured.
and for gawd's sake, if you must run Mytee crap, have a back up.