I think to some extent you have to have some kind of emotional attachment to really enjoy older titles, and tropico reloded is a good example of this in action. I cannot for the life of me get into Tropico, and that is a shame. There is nothing wrong with either of them, and one can argue that compared to the newer iterations the first tropico contains just as much, if not more depth to its mechanics. There are more of everything. More edicts, more graphs, information I'd really had liked playing Tropico 4 laying in the open.. And i still can't get into it. Mostly it is due to the clunkyness, newer games will spoil you like that .)
However, for what it is, and for what it should be expected to be when going into it, the first tropico really acts and feels like the later games, so much in fact that the later games feel kinda lazy for ripping so much of the old content rigth of. And for this it should be respected. If you want to experience the genesis of the series then get this, but be prepared that even if it is the same old Tropico you love and like, the keyword here is old. :)
However, that says nothing for the second game of the pack, Tropico 2: pirate cove!
It is completely different from all others of the series, not only due to its pirate themes, but due to significant changes to gameplay as well. Instead of factions such as nationalists and environmentalists the island populace is now divided into enslaved workers and pirate overlords (Note that some subgroups such as hedonists and gentry exist among the pirates, but it is very much streamlined between the groups).
Trade is marginalized in favour of raiding and rather than creating a self-sufficient island you now need to focus on getting piratically powerfull enough to take what you need through raids and buccaneering. It is a fresh and different playstyle compared to the other tropicos and making your island run effectively, juggling worker repression and pirate happiness is very different from the teasing and pleasing of different political factions and building effectively now has an element of demography to it as well since pirates enjoy anarchic environments and abhore order, while workers on the other hand need orderly environments to work effectively and escape easier when anarchy is high. It is great, and in itself a very solid strategy game. Also, good pirate-themed games are rare, so giving it a spin just for that is justified.
As you can see, my view of these games differ quite a lot, and this brings me back to the first point of the text; that emotions can make or break the experience. I never played Tropico 1, it is old and clunky and i cannot appreciate it properly. I did on the other hand play Tropico 2 as a kid. It is old and clunky, and I love it.
Thus: While I can reccomend Tropico reloaded for what it is, an old but iconic forerunner to a good franchise and a nice island management game with a pirate twist, i can only on a personal level recommend it for Tropico 2. Make of that what you will :)