Good topic. I have much to say about this, as I'm having this conversation regularly in my house.
My spouse (who also grew up quite poor) bills a certain amount per hour, and he has enough work to be billing 24/7 if he wanted/could. The way he sees time is: if I can outsource doing ____ for less than I charge per hour, it doesn't make sense for me to do it, as I will be losing money.
I can understand how hiring a gardener at 100$/hr makes sense to do if you get paid 500$/hr and gardening would take many hours from your week to accomplish and you hate gardening. Totally get that.
However, watching him live this concept out has made me realize that there is a huge flaw in this reasoning. In a vacuum it makes sense, but in real life it's insane. Basically because it means every minute has a price tag on it. Does that mean we never spend time on anything that makes less than us/is free/costs us money? Do we hire a dog walker and skip our daily walks with Fido because that walk is costing us jointly over a thousand dollars for that hour? Where does it end?
I chose fixing up ugly proerties as my job because I truly enjoy many aspects of the process. So I don't think I'd be happiest just finding deals and not having any part of the transformation of the home. Would I be wealthier? Perhaps. Happier? Probably not.
If you manage to do okay in this business or any business, you will find yourself faced with these very questions. And the answers aren't very clear. You might gain or lose money outsourcing, but how does shouldering the burden of something you dislike so much or letting go of something you really love cost you- not just financially, but personally?
I know my response is way more philosophical than your question. But my advice is to not forget the prize - freedom to live a full life. Do what you love. If you can outsource stuff you dread, do it and don't feel guilty about it. Make time for friends and family. Indulge in a hobby. Tile the bathroom if that's what you really like to do! For some it's a tedious task. For me, it's time to just listen to music, clear my head, and create something nice.
Because the sky is the limit in this business, it's easy to get carried away. You will hear a lot of people who are never happy and just want more and more and more. Reality? Money is a lot of fun. Getting that first big paycheck is exhilarating. And when you buy that thing you've always wanted and can't believe you can afford it finally, it's really an awesome feeling. Then you know what happens? You get used to that lifestyle. It's your new norm. You move to a place where your Mercedes Benz is now parked in a row of Rolls Royces. The toys lose their charm. The game never ends.