I just checked on Hotels.com and it looks like you only have 2 options: the Best Western and Holiday Inn. I've stayed at both and Holiday Inn is slightly nicer, but Best Western is more than fine. They're both around $125, but Best Western is a lot closer to campus. By a lot, I mean like 5 miles. Either way, yes, Olean does have Uber/Lyft, but there probably aren't too many cars. You could stay in Ellicottville, which is a small ski resort town about 30 minutes north of campus, but that's probably slightly more expensive.
You must 1000% get a Burton burger. Will you think it's the greatest burger ever? Maybe. Will you be pissed you waited 45 minutes for it? Probably. Either way, if this is going to be a one-off trip for you, absolutely go to the Burton. The owners of like 40+ years sold it last year to a group, financed by some Bona alums. I haven't been since ownership changed, but I imagine it's basically the same. It's not a place where you'll sample 100 NYS craft beers from the Adirondacks to Buffalo, but it's the best place to get a sampling of being a Bonnie. If you do want the burger but don't want to wait a million years, I'd recommend going about 2 hours before tipoff (it's 6:30 p.m. for SBU-RICH, so it'll definitely be open). The Burton will also be the epicenter for the postgame-2? a.m. 80s Weekend debauchery.
You should also swing by The Rathskellar, the official on-campus bar. So I don't start a B*ndwag*n-esque debate here, let's just say the Skellar has... inconsistent service and leave it at that. Even if you don't buy any food/drinks, walk down there for a couple minutes. There are some cool jerseys, photos and other displays.
I know, another place with booze, don't sound so surprised, but downtown Olean has a cool, new brewery called Four Mile Brewing. It's more of a craft place like you'd see in a city like Richmond. Great flatbreads and I recommend the Allegheny IPA or Pre-Prohibition Ale there.
Yes, there are some sober things to do in Olean/Allegany. Depending on how the weather is that weekend, you should walk around outside near Devereaux Hall. The architecture on-campus is gorgeous, so it'll be worth seeing (Richmond's is too, but ours is more Italian/Spanish, as opposed to UR's more classically English look? idk architecture like that I'm a Twitter shitposter that acts decent on A10Talk). By late February, you'll have a better chance of winning Powerball than guessing what the weather will be. Yeah, we get a lot of snow, but on February 24, 2017, it was 71 degrees on the Friday of alumni weekend! 71!!! That was about 9 months after it snowed on my class of 2016 buddies' graduation on Mothers Day... If you don't go to Ellicottville, you could also check out Seneca Allegany casino, although it's not exactly Vegas, Mohegan Sun or Atlantic City. There are some more outdoors things you could do in the warmer months, but in February, honestly the entire area is Bona-centric.
Finally, you won't get any shit for wearing Spiders gear, unless you dress up as Spiderman or something. If anyone starts making fun of you for liking Richmond, just bond with them over our mutual disdain for VCU. We always pull for you guys in the Capital City Classic...
This has been your Bona Commenter online tour, hope you go visit!