I quite often ask for discounts for stuff I buy especially when in a physical shop and armed with a smartphone that can give me an instant internet price to compare goods with. With regards to outdoor gear I have done this many times and in some instances to such a degree that an Arab trader would be proud of me. My question, as per the title, is how far can you push this and at what point does it become cheeky bordering on an insult to the vendor? Oh, and whats the ‘best’ result anyone has ever gotten in this way? For me it was 35 years ago when I bought my first backpacking tent. I went to an outdoor show and saw a one man tent for £45. I haggled with the chap and got it down to £38….mainly because that was all I had. Well not quite, I kept 10p for the phone call to my dad to pick me up from the railway station!
Saddlebags and Backpacks - a brewer's outdoor adventures 
Always haggle. You can’t insult a vendor, they’re there to make a sale and you’re there to buy something so the only issue is what is an acceptable price to the two parties. Traditionally, it’s 10% for cash but I always ask for more.
10% is ok, its just I know what wholesale prices look like so am more tempted to go in at 40% and work back to a minimum of 10% 🙂
Same here! Never hurts to ask.