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I rarely haggle, but on my next purchase I will. And I will buy a demo otherwise wait for a used bike on PinkBike. I don’t like eBay because they take so much money from the seller. I sold 2 bikes on eBay last year and got absolutely CREAMED on commissions. I’m doing demo-rides for my LBS and taking groups out for them since I know all the trails in our area so well. So I’m sure I’ll get a good deal on a demo bike.
As for everything else, I don’t ask for discounts. Especially not service and I tip big, always at least S10 and up to $40. I have a good relationship with all the mechanics and because of that, my bikes get fixed (unless parts need to be ordered) while I wait. I’m never pushy with them and I think that’s why they offer to work on it on the spot, unless they are super busy which is totally cool.
I would go 1×10 and replace your shifter, derailleur, cassette, chain ring and chain. I did this on a 2×9 bike of mine last year and it cost me $180 all-in (SRAM GX shifter & derailleur). I am sure you can get it cheaper now. The NX range is even lower cost. I figure for $150 you should be able to get it done. More than worth the money.
The 11-40 9-speed cassette in one of the links above alone are $139 before taxes/shipping. You can get a 10-speed Sunrace cassette with that spread for $65. And you can go as low as 30t on the chainring. A 30t chain ring with 40t low gear on the cassette gives you a pretty low ratio and you should be fine with that almost anywhere.