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Speaking as an SD owner, I'd tend to lean towards the Sub-Date as a watch with better resale value due to it's higher demand in the used Rolex market.
If you're only going to hold onto this watch for 2-3 years, the maintenance cost of an SD is negligible as you probably won't have too take this watch in for at least 10 years from the date of purchase (That is unless you do a lot of deep sea diving in the watch).
In terms of ruggedness of the 3 watches you listed, the SD would be tops for the simple fact you can go 4000 feet with it. The Sub only goes 1000 feet and the GMT a puny 300 ft.
The Sub and SD from what I understand have the very same braclet except the SD get's one whole link and the Sub only half a link. The SD has 5 links on one side and 9 on the other. Both have the extension clasp.
The GMT has the same links (don't know how many though) BUT, the clasp is different than the SD and the Sub. The clasp on the GMT II is smaller and has NO extension links hidden in the braclet.
The SD and the Sub have a triplock crown. GMT II does not which is why it has a lower depth rating.
In my opinion, both the SD and Sub are more rugged than the GMT II and of the SD and Sub, the SD is more rugged than the Sub.
But that's just my opinion.
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