Welcome, indeed, stevekoe!
Since you know where you travel (Dallas and New York/Long Island) consider that you will be staying at the same properties over and over. Your opinion of the specific hotels will matter alot. Consider searching the Marriott and Starwood forum (and the rest of the web) for reviews of these properties.
Randy makes a good point in asking what your reward goals are. Do you want hotel stays or airline miles? And what kind of stays are you looking for?
Finally, what benefits are most important to you? If suite upgrades are king, there's little question that Starwood will be more to your liking. But if free breakfast is king, things may be different...
Also what were the problems you encountered with Hilton? That may give a window into which program you should consider.
Finally as to who to request a comp from - at least with Starwood comps are once in a lifetime, so I do think you should only request the comp if you know you'll requalify.