If the hotel you are talking to is ready to make crazy things at crazy prices, they will answer “yes” to anything that can be solved by throwing money at the problem.
On the other hand, for hotels that don’t deal with lunatics, they will refuse to deal with you the moment they smell your problem is bullshit or unreasonable.
In the end, I’d think false positives would be extremely frequent with that approach.
I worked one summer at a five-star hotel in a ski town in the rockies. At various times and for various clients (typically on short notice) we (1) hosted a banquet for a former U.S. president that involved locking down the hotel with the secret service, (2) drove 2 of the hotel's SUVs 100+ miles round trip to buy dozens upon dozens of suitcases for a member of the Saudi royal family, (3) turned a conference room into a fiber connected operations center for a team of high-frequency traders that was visiting from NYC for two weeks.
I am certain that the hotel manager would have told all of these guests that we would absolutely find a way to handle their requests, no problem. And we did. That is part of the reason they were at that particular hotel in the first place.
Idk, people ask, "CAN YOU MAKE THIS APP?", I always answer, "I can".
If someone asked me if I can build some robotic thing, I'd answer "I can".
If they asked me "Can you build X in Y Weeks?" then I need to know the project.
I have been able to do pretty much everything thrown at me. The biggest question is how long we have and specifying what we actually want.
I can work the hours, but I'm not sure the logistics and ergonomics of transporting that quantity of material."
Look at it from a hotel manager's perspective. Let's say he normally is willing to negotiate, so he'd want to say "That is difficult because of X - would you consider Y instead?" But he's also wise enough to see he is being tested, and is this is triggering all types of alarms in his head. He's had his own repertoire of bad clients, and so instead of negotiating, he'll put him through his own tests. He'll just say "No" and see if the client is willing to negotiate or is adamant, and see if the client fails the test.
I'm not in the business so I can't say for sure. Sitting here, I find it to be a poor assumption to assume the client has the upper hand (because he has business to offer and money in hand) over the hotel manager - and this person comes off as assuming as much. Consider that the hotel manager may have other options, or that this type of a deal is a net negative for him (even if the hotel is well compensated for this, there are non-financial costs).
You ask if a certain task or project can be accomplished and the people who say yes without any hint of a problem are almost certain to be the people who let you down.
The guy who asks for more information and, maybe, presents you with reasons why your project isn't so simple as you thought is much more likely to deliver.