Hilton Strategy
 

I usually pay almost no attention to hotel points. Most of my travel is to Las Vegas, where my "go-to" hotel is not part of any loyalty program. Other times when I have to stay in a hotel it's usually one night at a time and I book on Hotwire. However, about a year ago I anticipated a situation where I might be traveling to a somewhat remote area (not like central Montana, just an area where there were no hotels of any quality within 10-12 miles) somewhat regularly and there was a Homewood Suites, so I got the entry-level Hilton credit card. I never did make that stay. I still have the credit card and I make sure to use it once a year or so to keep my 100K Hilton signup bonus points from expiring.

This summer I am going to a convention where I will probably stay at a Hilton for 10 nights at around $190 a night plus tax. So if I use my card, and given the silver status that comes with the card, I guess I will get around 20K points (assume $200 a night for convenience) for the stay and 14K points if I put it on my Hilton Amex.

It's possible I will go to more conventions - specifically, they are the national bridge championships (bridge as in the card game) and are held 3 times a year.

It's probably also worth mentioning that the bridge games start at 10AM, which to me is the middle of the night, there is an hour break for lunch, and they finish around 6:30-7PM. Ideally I would like to just change my circadian rhythms for a week and a half and go to bed at 11 and get up at 7:00, but I don't know if that will work. I also take a lot of time to wake up properly. When I go to Vegas, I usually wake up and make a cup of coffee, put on some sweats and go to the casino for a couple of coffee-and-kahluas, eventually come back to my room and take a shower and get dressed. So I'm not sure how much use I'd get from a free breakfast, if indeed that's available.

My question is, is it worth upgrading to the next higher level of card? I think it has a $95 annual fee, a 130K signup bonus, and grants gold status. There's no way I would spend enough on the card to get upgraded to diamond status. I think for this stay alone it would get me 14K extra points.

If I got the basic Hilton Amex a year ago, would I be eligible for the new SUB?

I would be unlikely to use the card for everyday spend, as I have better cards for that. (One of my Amex cards gives 2x points on almost everything, and with the points rebate on travel I get from another card, it amounts to about 3.05% cashback.)

Is this worth the bother? Are any of the gold benefits worthwhile for an occasional traveler?

The main benefit for Gold over Silver is the daily food and beverage benefit ($10 to $15 a night or so, depending on the hotel). If you are going to eat breakfast in the hotel anyway, then the card will pay for itself with this credit after ten nights.
A secondary benefit relates to the points earning. Gold status earns more per dollar spent than Silver, and the $95 credit card earns more per dollar spent at Hilton than the free card.
If you are going for the $95 card and want the sign up bonus, just apply for the new card rather than upgrading the old card. You can have both cards.
Also, before your trip, check for Hilton bonuses - there is often a "double points" promotion, or a promotion that provides extra points per stay or per night. You have to explicitly register for this type of bonus.

I had to book the reservation on the convention website, so even if there were a bonus it probably wouldn't apply if not booked on Hilton.com. But I'll keep my eyes open.

You don't say if the other conventions you're attending will also be at Hiltons. But if that's the case, then I think I would do as jdbeckett suggested above. Get yourself another bonus.

Also, it's surprising how you can easily move up to Hilton Diamond. They've lowered the threshold post-Covid. So with all these conventions, you might find yourself at a new status level.

And then the question is when and how to spend all your points. I'm blowing a chunk of mine at the Hilton Molino Stucky in Venice this summer.

I think you can still get points (and bonuses) on reservations not booked directly with Hilton. Worth a try. But you probably wouldn't get your Gold benefits.

Nice rooms and location.
Free river taxi
Excellent Diamond lounge food and drinks.
(However overzealous staff when I left the lounge holding a glass of wine. He actually ran into the elevator and grabbed it from my hand. Free fruit basket and bottle of champagne because of this.)

Small rooftop pool for posers and/or screaming children. Great view of Venice. Do not expect to swim when busy. Refreshing though.

My favorite pizza is in Venice.
Casin Dei Nobili