However, the thought of making all these ridiculous offers is embarassing to me. Sure some people will bite, but it's rather insulting to the rest and very annoying.
You're actually more correct than you know. Low-balling to the point of insulting the seller puts them on the defensive, and gives you instant "idiotic cretin" status in their book. Once that's established, getting something bought at your price (or sometimes even a reasonable price) is far less likely. You're better off deciding on the price you want to pay, offer it, and don't budge. If it's reasonable and within what most people would expect as far as price range for the object in question, you're much more likely to get it bought.
I can list you example after example of people who shot themselves in the foot trying to buy a house by low-balling the seller with some abysmally insulting offer. Those who actually succeeded in buying the house usually ended up paying far more for it than they would have if they'd been reasonable in their first round of negotiations. To a person the sellers all said the same thing, "I would have sold it for X, but that guy was such a jerk I wasn't going to let the house go until I made him pay for being such a dumba**."
I have a perfect example of how
to be a successful negotiator. I have some investors who buy two houses a year. In every case they make an offer an then don't budge. Ever. Yes, it's usually slightly under the comp value, but only a few percent. Even though the offer is less than the average for homes in the area, but it's close enough to make the seller nervous about not taking it. Their success rate is almost 100%.
Sure, there are guys out there like the one you mentioned. They will shotgun offers on everything hoping to catch those people that might be in a severe financial bind. They can then flip the item at their leisure. But I haven't met very many who can justify the time involved in terms of actual income. The ones who can sure don't do it $200 at a time, though. Their numbers usually have a few more digits left of the dicimal place.
Brad