Hi Stacy,
As i have already signed up for Regent, my views may be a little biased so take it how you will...
1) Regent is certainly not as well-known as some other 5 star hotels but lets put it this way, how many elderly folks know which are the 5-star ones and which arent? Also, i think that they will give the same amount regardless, unless u hold it in a restaurant, in which case they will give less.
2a) For a 5-star hotel (believe me i have checked this out...they are related to 4 seasons, which i am sure most older folk will associate with good service) , i think that Regent's pricing is reasonable. Do not forget that it is NETT pricing. I was quite shocked to learn that Pan Pac and Oriental and even Marina Mandarin charge similar if NOT more than Regent.
By the way i too am quite apprehensive in how much i might stand to lose but no point worrying about what i cannot control.
3) Food wise is a moot point because one man's meat is always another's poison. I am sure that if i like one dish, someone else will say it is bad so u cannot please everyone. However, you can at least be comforted that Regent (unlike Orient, Marina Man and PanPac and several other well-known hotels) have an in-house Chinese cuisin restaurant...Summer Palace. Granted it is not as famous as Li Bai from Sheraton but it is certainly better than banquet chefs from those hotels aforementioned. trust me i have eaten at the Fullerton, Ritz, Marina, Orient and the food is all about the same...
it does not mean Regent will be better BUT i dont think it will be worse...
4) Marriot's location is indeed more central BUT peak hour traffic is a headache going in there. Same goes for those hotels in the Marina Man/Suntec blocks. Also, remember that the parking lots are also taken up by shoppers so Marriot may not be able to give u as many complimentary carpark coupons as say, the Regent...but i may be wrong here.
Location wise, i tend to think that Regent's location is ideal because it is still on Orchard Road, but away from the maddening crowd...Would u consider Shangrila lower class because of its location? Right...Besides, by the time your wedding comes, St.Regis Residences will have been built right next to it and people can sense it is an upmarket place and hopefully dig a little deeper in their pockets...
5) Personally, i like Regent because your guests actually have a place to sit (TEA LOUNGE) if they arrive early..particularly the older folk..other hotels only have standing room which i find a pain, especially since dinner usually starts 8plus and folks who arrive early have to stand for quite a bit...Also, the themes are pretty unique and the packages are quite comprehensive already...
End of the day, u make the decision and hope for the best...
hope it helps...