Hey!
It will, at least for the most part. The output would be something like this: Koh Samui, Koh Samui hotels, Koh Samui travel, Koh Samui travel tips, Koh Samui travel advice, Koh Samui tavel guide, guide to Koh Samui, travel Koh Samui, visit Koh Samui, holidays to Koh Samui, Koh Samui holidays, Koh Samui vacation, Koh Samui vacation rentals, Koh Samui vacation guide, Koh Samui hotels, Koh Samui villas, Koh Samui villa rentals, Koh Samui tourism, Koh Samui vacation packages, Koh Samui nightlife, Koh Samui weather, Koh Samui maps, Koh Samui resorts, resorts in Koh Samui, temperature in Koh Samui, Koh Samui island, the island of Koh Samui, Koh Samui beaches, Koh Samui resort guide, information about Koh Samui travel, info about Koh Samui and a lot more...
As for your second question - it will generate keywords for each URL separately, but we might limit those to 20-30 variations per URL - depending on how many URL/keyword sets there are. For example, if there were 20 URL/keyword sets for the deep linking blast, there would be no point in pulling over 30 or so keywords per URL, because some would never get used.
Let me know if you have any other questions!