I dealt with this before, I wasn't flipping cars, but it was large machines.
One time I found a great deal and was the first person to arrive (the seller said he would not hold it for anyone and whoever showed up with the cash first, would get the machine). I was literally a few minutes ahead of the next buyer. I ended up getting the machine, but the second buyer showed up and saw me loading it onto my trailer, he didn't look too happy he had just missed out. Fast forward about a week or so later, I fixed a few of the mechanical issues and relisted the machine for 1.5X what I bought it for and the first person to respond and show up was......you guessed it..... the same guy from the day of the initial purchase haha.
Great story - so did the guy buy it from you?
He did not. It was actually still a good deal for him, he lowballed me, I turned him down and sold it the next day to a different person for my full ask. I honestly could write a very entertaining novel on the experiences I've had on Craigslist. 2007-2011 was the golden era for this specific market. I made a lot of money flipping industrial machines, mostly commercial lawn mowers during this time. I was finishing high school and in college during this time and felt rich with the money I made haha. Learned a lot of negotiation tactics along the way. It's one of those small markets where I knew literally more than 99% of the population regarding the market (after hours and hours of research) for these machines & their value both locally and/or how to sell them online regionally (although 90% was local), how to fix the problem, etc. I acquired this knowledge as I'm a reader/research type of person and I started a business mowing lawns in my neighborhood and grew it rather substantially once I got my license.
Here are 2 stories... The first is my first deal which is how I inadvertently came up with the idea and the second being one of my better money makers. There are many more entertaining stories, but here's a preview.
Story #1 - How it all started - 2006 - I'm a sophomore in high school, 15 years old, can't drive yet, busting my hump mowing lawns in my neighborhood to make money. There was a large saturation of elderly people in my neighborhood growing up, so I would push my equipment around the neighborhood each week and had I believe, 10 yards at the time, all of which were in walking distance, it was a great start. I charged between $30-$40 per yard, so it was good money and an even better learning experience.
I decided I needed better equipment and referred to the local newspaper and found a "Commercial 32" Toro Mower" for sale for $750 in the Farm & Garden classified section. There were no pictures as it was a minimal 3 line black and white text ad, so I called the seller and asked for more info, I got the model and serial and started my research via Google. I determined it was about a $3,000 machine new and my Grandpa drove me to check it out. The seller was a nice older guy, who bought a new tractor and was just looking to part with this mower, said he "was sick of walking". It was in great condition and after a brief chat, I bought it for $650. I used it for a few weeks and then stumbled on to .... Craigslist ... for the first time in my life.
I had no clue how Craigslist worked, but I cleaned the mower up, sharpened the blades, changed the oil, put new filters on, and confirmed everything worked as it should, and took fresh pictures and posted it to Craigslist. I decided to post it for $1,000 more than I paid for it at $1,650 not thinking anything would happen. The next day I received 2 calls, the first caller said he exclusively used this exact machine as it was most efficient for his route as all the houses had narrow gates and he needed another mower for his fleet asap. He said he was very interested and could come over that day. He showed up, looked it over, complimented me on its condition and gave me my full ask. I kept my composure, but when he drove off, I couldn't believe I had just made a $1,000, it felt great and motivated me to continue hunting for opportunities.
Story #2 - One of the best money makers ... I believe it was 2010, I was back from college for the summer, working an internship 3 days a week and mowing sun up to sundown the other 4 days. It was a memorable, summer, I worked literally every single day of the week and prayed it didn't rain, somehow it rarely ever did. I'd start at commercial buildings at sunrise and mow residential houses until dark, I had a great route. I was following up my 10-12 hours days outside up with 10-12 hours days at my internship, it was the most I've ever worked during a summer.
Anyways, one of the days, I finished a bit early and needed to pick up some parts for my mowers. My normal dealer was out of stock, so I went to a different dealership I rarely visited to get the parts. I knew they had a "Used" section and would occasionally take a look, but never found anything, anytime a Dealer is selling something, there is rarely any room to make money anyhow... It was a Dixie Chopper and Exmark dealership I believe. Anyways, I was already there so figured I'd see what they had. I noticed an orange machine in a back corner, the only orange machine in their shop, it stood out. I asked the salesman about it and he said they got it in on a trade in from one of their big customers and that they don't sell Scag, but didn't want to turn the customer away as he had an entire fleet of Dixie Choppers he had just upgraded and traded mowers into them, this was the odd ball mower, he was a big customer for them. One of the tires was flat, the mower was dusty, and the pull cord had broken. I asked him what they wanted for it and he said $700. He left me and my friend to go tend to another customer and we investigated further. My friend (who was the mechanical one, not me) believed there was compression and the engine would definitely turn over. I knew it was a hydraulic mower (more expensive high-end machines versus belt driven machines) and found the model and serial. I called a Scag dealership and they determined, based on the model and serial that it was only 4 years old. I knew new machines like that sold for about $5K, so this was looking like a gem... We inspected the mower further and it looked really good, and we could tell it hadn't been used much (I'm guessing was part of a fleet and only used on back yards, so mostly sat on a trailer all day).
I approached the salesman and proceeded to complain about the cost to replace the tire, the pull cord, and other minor things I could come up with that were true, but were mostly cosmetic ("the mower is soo dirty, when was the last time it ran", etc.). I asked him how anyone could even load it if they bought it as the tire was out. He offered to get their forklift and lift it onto my trailer, I offered him $500, and he agreed. I stopped back at my normal dealer on the way back and bought a new tire, pull chord, filters, etc. for about $125 all-in.
The mower looked brand new once it got a proper cleaning. I probably didn't even need to replace the filters and plugs, but I liked to spend some extra money and make the machines in perfect condition before selling (which literally NOBODY does, it blows my mind how people are selling something for thousands of dollars and don't even clean or take a decent picture of their product), so I always spent the money and time to do this. There wasn't any comparable mowers in my town, but after some research, I listed it on Craigslist for $3,100 or best offer. Additionally, I never sold anything until I had thoroughly reviewed all the functionality to ensure it was working perfectly. This proved to be a good strategy as potential buyers couldn't negotiate the price based on what they had to fix, b/c I had already reviewed and corrected everything that needed to be fixed. Right after I listed it, I had to leave for college. I had a few people call and offer me $2,000 which I passed on. After about 2 weeks, someone showed up and bought it for $2,800. My friend met with the buyer as I was out of town and I gave him piece of the profit for his help.
There are many more stories...including 1) Selling a Machine to someone that doesn't speak English 2) A standoff (when buying a piece of equipment) with another buyer that ended up with a bidding war and ultimately a coin flip to determine who would get the machine with a pissed off second potential buyer, etc.