To be fair, I’m more interested in your thoughts and perspectives on this, than I am in finding a specific answer:
That’s the best way to look at it; because there is no specific answer and it will be the same questions you’ll be asking yourself in years to come.
1. Friends and family: That one was very difficult for me in the beginning, but as I grew my business, my friends and relatives began to realize this was my living and respected that by not asking or expecting me to build things.
With that being said, If asked to build something for a friend or relative, I try to do it as a gift and sometimes I have to gracefully back away if I simply don’t have the time.
2. As far as a project that may require a new tool, I usually chalked that one up to growing and giving myself the ability to advance my woodworking. Years ago, I did bid on a job that was restoring a century home that required turning 69 spindles to rebuild the gables. In my price I figured a new duplicating lathe since I decided if I tried to turn 69 spindles would be like repeating a story 69 times. (the last one is never excactly the same as the first). I did get the job and I did get a new lathe. lol
3. Sometimes it’s OK to do a job more for the experience than for the profit, but since woodworking is a never ending learning experience, that can be a slippery slope.
For me; owning and operating a custom woodworking business for 27 years, it didn’t take me long to realize I had to make a profit to stay in business and nothing will take the joy out of woodworking faster than giving up all your time for nothing.
If you’re doing woodworking only for the satisfaction of building the projects, then keep it strictly as a hobby and never worry about charging for anything other than materials.
The hardest thing for any woodworker, is trying to bridge the gap between being a hobbyiest to being a professional woodworker making a profit doing woodworking. _ Everything in between is a struggle trying to justify what and why we’re doing it._
The decisions you make on how to handle each senerio is whatever feel right for you at that particular time.
Good luck
John @The Hufford Furniture Group