Hilton HHonors - Can Gold get suite upgrade if pay for Executive Floor?

I have always wondered if, since Gold gets an upgrade to the Club level and
access to the lounge, if one were to pay for the club level, would the hotel be
likely to upgrade to a suite?

The answer definitely is "it depends."

I did just as you suggest - reserved executive floor at the Conrad Singapore on a 3-night paid stay, and they moved us to a suite on the second day (it wasn't available at check-in). I was a Gold then.

Officially it's not listed as a benefit, which is why YMMV.

Upgrades are to the Executive floor, not to a higher level than what paid for. There are exceptions, I have paid for executive and gotten junior and regular suites in the past. But who knows if they would have been mine otherwise.

You can always ask for upgrades to suites but if not given you can not really see that as a non-compliance issue.

I have booked a "regular" room and have been upgraded to a suite on the Executive level at times and other times I have booked a "regular" room and have only been given access to the Executive level lounge. It all depends on the traffic. :)

I have been forced to pay for an executive floor room when that was all that was available. I have been offered an amenity in place of the free breakfast that I paid for. In one Hilton it was a coffee mug, in another Doubletree it was a lint remover. In no case was I upgraded to a suite. I think the principle is the same as the following quote from the Membership levels page on hhonors.com:

"when in hotels or when paying a rate where a complimentary breakfast is a benefit for all guests, Diamond VIPs will be offered a special amenity as an expression of our appreciation. "

I am in suite at the Singapore Conrad right now, I booked an executive floor room and was upgraded at check-in.

I have been upgraded to a suite a few times at other hotels as well. But more often I get the room I reserved. I try to never expect the upgrade, and am then happy when it does happen.

If I really need a suite, like when I am traveling with the family etc, I book a suite. That is the only way to be sure to get one.