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Pirates are my favorite theme, they both put me into my dark ages and brought me out, I went into dark ages because they were my favorite theme and I realized they would not release any for a LONG time, then randomly I saw in a catalog (that my little sister was still receiving) that they were releasing the Imperial Flagship, well that brought me out of my dark ages.
I assume pirates will be on hold for at least 5 years (just a random guess), maybe even more if they continue making PotC sets. I think it would be pretty hard to market both sets at the same time.
I too am a huge Pirate ship collector, I suggesting looking at bricklink and getting a base price for the ship or ships your looking for and then look at ebay. I did a lot of stalking on ebay before I would buy any ship, usually watched items list and sell for around a month and then get an idea of what my max bids would be, if they consistently sell higher than bricklink (not often in my experience) go with bricklink. If not try to win a auction on ebay with that in mind. Pay close attention to the figs tho, for me I really wanted to get 100% complete sets, but some people don't know what figs go with what ship and that can be a problem with some vintage sets that have rare figs. So look closely and look for what I called "deal breakers" Such as missing pieces that are rare (the jolley roger brick on Skull's eye schooner, yellow bird on Caribbean clipper, etc.) you may think you're getting a good deal on the ship as a whole, but if its missing those kind of pieces it may be hard to get and could run up your bill getting them from bricklink.
Sorry if I spilled too much info, its not often I get to talk about Lego Pirate ships. Like I said they're my favorite sets, and myself have been working to collect the 10 pirate theme ships (excluding PotC).
Yeah thats what im planning to do, I bought Imperial Flagship for £108 on ebay plus shipping which was in total £130 i think on pixmania in total set with shipping goes for 120 so its still not too bad,
I bought Black seas Barracuda for £80 pounds but it was not in perfect condition.
I really like big sets, but unfortunetly Lego is very expensive hobby ;)
See here for a helpful list of terminology you'll find when re-entering the hobby!