I like to take it slow and buy when the budget allows power tools and hand tools. With hand tools I wait it out and buy the best I can afford. I learned that lesson years ago. My first year carpentry teacher and the old guys at work always said ” Buy the best you can afford,you will retire with them same tools” And I plan to do just that. It also taught me to look after what I had. So with this whole hand tool revolution I am going through right now it still makes the best sense. With all the great newer options and reputable companies out there anything I buy these days is usually new. I did buy a bunch of old planes 15 or 16 yrs ago at an auction and have been refurbing or turfing them for years.
As for power tools I bought used. The new stuff just doesn’t do it for me. Lately they just sit in the garage getting covered in dust and stuff anyways. Might just sell a few off so I can afford some hand cut rasps.