I'm kind of looking for arrows pointing to where the land mines are.
I think I'd skip HF for my mainstay tools EXCEPT where I had carefully specced the exact tool I needed to buy and HF had a tool that EXACTLY met that spec or exceeded it. I just bought a Milwaukee 5625-29 router and it's a real eye-opener. Can't get anything like this at HF.
I also think I'd downplay my willingness to do custom work and put more effort into building inventory to sell from.
And I'd also give more thought to cost tracking so I'd be collecting needed data from day one.
I find that I have a LOT of pen blanks cut from unremarkable wood. Skip that ... anything that isn't eye candy is firewood.
I've got others ... but I'd like to hear from you.