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So the guy who has a few wives die on him on earth and is sealed to both of them is going to have polygamy in the afterlife?

Yes, so long as he makes it to the top-tier Mormon post-world kingdom (eternal polygamy isn't for the spiritual middle or low-class neighborhoods). The second proviso is also that the sealing "for eternity" ritual be done in the temple. (Some LDS men have been consecutively married, but only were sealed to one wife "for eternity").

What about the guy who dies before his wife? Does he lose out?

Yes. The eternal spiritual polygamist gets the "head start" for churning out millions of spirit babies with multiple eternal sex with multiple eternal wives in populating their own planets. (Of course, Mormons tend to be silent on the "eternal sex" thing...but because of their emphasis of a Mormon god who has a physical body, they believe they'll become gods & emulate him.)

So what does it mean to "emulate" the Mormon god in this manner? (For that, let's turn the pages to Brigham Young himself, followed by LDS apostle Bruce R. McConkie):

"When the time came that His first-born, the Saviour, should come into the world and take a tabernacle, the Father came Himself and favoured that spirit with a tabernacle instead of letting any other man do it." (Journal of Discourses, Vol. 4, Page 218.) [IOW, the Mormon god ventured from heaven to "visit" Mary, "favouring" her with his "tabernacle" vs. "letting any other man do it."]

"The birth of the Savior was as natural as are the births of our children; it was the result of natural action. He partook of flesh and blood -- was begotten of his Father, as we were of our fathers." (Young, Journal of Discourses, Vol. 8, page 115).

McConkie: "There is nothing figurative about his paternity; he was begotten, conceived and born in the normal and natural course of events..." (Mormon Doctrine, p. 742.)

There ya go. Other than a supernatural being supposedly being present, nothing really "supernatural" occurred when Mary was impregnated. Young said it was as "natural as are the births of our children"; McConkie said it was a "literal paternity" (which would mean DNA & all) in which Jesus was "conceived...in the normal and natural course of events."