I will not pay in advance or pay a deposit for a meeting or an O/N. And I don’t think I’ve lost any meetings (at least not ones I regret ?). With a guy I liked too much I did pay an advanced deposit once, and happily everything worked out. (he was traveling and I wanted him to change his schedule to accommodate mine and leave a city earlier than he had planned and get to his next planned stop a few days earlier - so it made sense to me to show some good faith and send him a deposit).
I will pay in advance for airfare/travel when I ask someone to travel to me. Note - I will pay for the ticket, not give $ to them to buy. And I must say, trusted regulars have generally paid for the travel themselves and I reimburse as soon as we get together (for travel as soon as we meet, pay for time at the end).
I agree for extended time a deposit may make sense, but you can Venmo $ when you meet as easily as ahead of time. As has been discussed, it’s a matter of trust, which is why I prefer to travel to him for a initial meetings and only after we have some mutual trust get him to travel to me.
as with many things, there is a range of options and a range of circumstances- no one right answer for all cases, but, ceteris paribus, be cautious.
steve