I'm sure after I give you exactly what you ask for you will still flame and hate. I hope not, but we shall see....
You want to hear "loopholes that don't exist anymore"? Here you go-
1- MWSE. Mid West Stock Exchange had a horrendously antiquated order execution system in the late 90's. They would sometimes "get frozen" while posting an offer. If MWSE was the only MM on the offer, you could keep SOES'ing him and they were obligated to keep filling up to 1000 share orders until they lifted. You could pound them then they would have to buy back all the stock they sold you immediately an 1/8, 1/4, 1/2 point higher.
2- ECN arbitrage. You used to be able to cross the market using the ECN's. Sometimes when a fund had a huge buy or sell order they would cross the market on ISLD or INCA by quarters or halves and you could literally max your buying power buying everything in sight and immediately sell it to them. It was risk free $$$. Happened all the time.
3- "Backing away" prints- You could "Select Net" through the NBBO and hit MM's. They had 10 seconds to fill your order or they had to lift their quote. Very often they would hold your order over the allotted time and lift without filling. You could then call Nasdaq operations (within 5-10 minutes if I remember correctly) and they would rule on your complaint. If they ruled for you, you were given the choice to take the fill or not. Back then guys would get backing away prints and be 5, 10, 20+ Points in the money...and if the stock went the other way you decline the print! It was insane.
4- REDI, STRK, BTRD prints- in fast moving markets the shitty ECN's would "get clogged". They couldn't keep up with the volume and you could get fills at prices where the market was at 20-30 seconds earlier. On the surprise rate cut days REDI prints would come back with fills from 2-3 minutes earlier prices. I got three 1000 share fills in SUNW almost 15 points in the money on that early April 2000 afternoon crash and rebound day.
5- Goose the market- you get long a boatload of stock in a quiet market then throw size bids on Island and Instinet then start SOES'ing the MM's off the ask. You then sell all your stock to the lemmings thinking there was a buyer....then you flip short a truckload, pull your ISLD/INCA bids and post size offers. Everyone would panic out, they would hit all your bids to cover your short. That worked great during slow lunchtime hours and summer days until ECN rebate trading took off.
You guys who keep hating just don't understand.
I get it, it's hard to imagine how things were during that period unless you were a part of it.
Kids right out of college in t-shirts and shorts on single screen monitors with crappy charts and slow cable feeds were printing cash.
It really was the Wild West.
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