Dear BoSoxFan:
Congrats on the "new lawyer". I was once a new lawyer. Not that I'm an "old lawyer" now... just more experienced
I am both SPG Platinum and HH Gold, although this "bout" of HH Gold has been comped. A lot of what I found lacking with HH has been "improved" such as point accrual on various rate types, etc, but I have never received any appreciably upgraded room or other special service as a HH Gold, and I have been one during 2 different time periods.
HH, however, is a good "back up" to SPG and at least they will keep you as a silver in your low activity years (or should anyway)
SPG on the other hand seems to have the best customer service around. Even though I can't receive additional miles with stays (as I could under the old Westin program), and had to live through a myriad of bugs in the new program last year, their customer service dept has always tried to remedy problems, including having a special dept. to work out "issues" after disastrous hotel stays. Although my "suite upgrade" rate seems to be below average when listening to some of the other Starwood posts, I do usually receive some sort of upgraded accomodation. Finally, with your travels, you should make SPG platinum and then you will get a "concierge" who you can call, even if a corp travel dept makes your reservations, who can contact your hotel prior to arrival with any special needs, upgrade request if available, and so on.
I am also a member of Holiday Inn (Priority Club), who refused to comp me even their lowest level of status. However, as they have decent affordable accomodations in a few places I go, I just let the points trickle in. Eventually I will have a free night in a motel somewhere.
You will also find soon enough that other hotel chains may comp you some status because of your CO.