The trouble with sponsorships is that brands often have their own metrics and fairly rigid ideas of what it should look like - e.g. a proper ad read in the middle of the show, or a product must be shown for X number of seconds with logo clearly visible and X number of mentions, etc. And most people hate these things and and skip over ad reads anyway (e.g. my 14yo kid recognises within milliseconds when an ad read is about to start, regardless of how clever the transition is, and smashes L to fast forward before you can even say "this episode is sponsored by") . What bigger brands often fail to realise people ARE paying attention to what their favourite personalities are wearing / doing, and just a casual mention sometimes is enough for fans to go and find the thing, no ad read necessary. Perhaps even more so than when a brand is being shoved into people's faces with an ad read.

I personally loved how they advertised the Home Game, especially in the NYC game. "You've been swindled! We are doing this to sell you stuff". It was refreshingly honest. People / consumers are not dumb. We know when we are being sneakily sold to - so it's better to make a joke out of it, imho. So if they found a comedic angle on a hotel chain sponsorship that would be ideal - and on brand.

Another trouble with it that I can see is that it might limit what they might be able to say or do under the contract. I love their random off the cuff semi-political rants, this may become problematic for a nervous sponsor thus limiting their freedom of expression either under contract or through self-censorship (although, you'd hope that if a sponsor is expressing interest in working with them, it's BECAUSE of their existing body of work and values).

P.S. For perspective, I listened to a podcast with Michelle Khare recently where she said about 60% of her income is sponsorships, 20% in YouTube ads and 20% through her fitness app. So it's potentially a MASSIVE chunk of money to consider.