I’d just have a frank discussion with him. “Hey tree guy/gal, I got 3 estimates but if price wasn’t an issue I’d go with you immediately, but price is always a factor so…do you have any deals coming up soon, buy two get one free, back to school, pre winter storm, etc? Or is there any prep work I could do myself that would lower the cost, or in that vein, any post clean up I could do myself?” And if after that the price is still firm ask, “ if you had to remove a tree and your company wasn’t available, is there another company that you would feel comfortable calling?” And if by chance the price is lowered and they do the work, have coffee and donuts or pizza and waters set up for them when they finish.

This can be tricky if one is naturally not comfortable negotiating the price (and that would be me, unfortunately). The approach in the previous comment sounds great to me. Wishing you good luck!

Just simply make the one you want a counter-offer. It's like dating; all he can say is "No". And he won't be offended. Maybe more like negotiating with a hooker than a date, but no hard feelings either way.

If they don't have to haul the cut up trees away, you can also save.

Thanks everyone!