(Perhaps a better analogy than the age of sail is the Mediterranean piracy of the Greek and Roman eras? Anybody with some bg in that might be able to shed some light...)
A note about pirates in Traveller - if there are rules for designing ships with stealth or masking of any kind, pirates will be all over this tech like black on space. And smart pirates will hang out in Oort clouds behind ice balls with minimum power for days waiting for the right conditions (planetary bodies obscuring the authority's sensor arrays, solar flares bleeding out PEMS, hiding in the tail of comets... who knows.)
Evading sensors and establishing bases in unusual places are the only ways one could have intra-system piracy flourish. Disguises like the JR would be one route. Using a freighter as a disguise for a fighter carrier would also work. As you guys have discovered, it depends on the rules system you use - the range of sensors, the availability and reliability of stealth tech, and the other variables already mentioned.
Piracy all comes down to the level of policing in an area. Space - both intra stellar and interstellar, is a very big place and no empire, no matter how well established, can cover it all with defenses adequate enough to keep out cutthroats. There is always a new frontier or backwater.
Another factor in the economics of piracy is poverty. If you have an area where the interstellar economy is failing - very rich rich, very poor poor, there are weak local governments, the belters are out of work, the Imperials or someone else is taxing too much, etc. - then you will have more people willing to risk everything to hit the big time.
Piracy isn't an isolated incident. It's a social phenomenon. A pirate or pirate fleet attacks, the SDBs and fighers scramble, the pirates are driven off, but another attack comes the following day from another set of pirates, and on and on . The take on raiding a whole system is so big, the law of averages state that some will be successful sometimes. It's just like robbing banks in the wild west or the 1930s.
Trotting out these one-time scenarios as "proof" that piracy is impossible isn't exactly the best way to test the feasibility of piracy in toto. Though I do agree with Whipsnade that piracy looks a lot different than it did in the age of sail. In my opinion it looks cooler.