I am in a similar spot - or was up until recently. I think it is good to go in with a plan and you can save you money long term - although it gets to a point where it is easier for you to do something to make that money and then just pay someone else.
Here is an example:
Just recently I decided to insulate my basement - it would take me a day of cursing, sweating and complaining that my back and knees hurt for the next 3 days for me to do it myself - so I reached out to a guy who I know that works for a company doing this sort of stuff everyday and asked him what he would charge. He responded with an absurdly low rate - to which I said that is too low - I ended buying him 2 tires he needed (I work in an automotive shop as my 9-5) and he did the work.
I can do a brake job in under an hour if I am hustling and make 200 dollars of profit there - so I would rather do a brake job and only spend an hour of my time to get the money needed to pay for the insulation labor.