be sure you know what she likes. Many providers have wish lists or the like on their web sites that can guide you.
One more tip: don't give flowers unless you're sure she wants them. I know several providers who don't like gifts of flowers.2 questions, really.
First, after how many visits with a provider would a small gift be appropriate? I'm thinking a bottle of perfume for a provider I've only seen once could be misconstrued...
Second, I am seriously considering an overnighter with what I consider my "regular" provider. Would taking her to dinner and possibly a little shopping be too much? I'm planning on reserving a deluxe hotel room with a hot tub and in-room breakfast.
Thanks in advance for the help.
I like to give gifts too, so I know the first time is a little like "Uhh... will I be weird for doing this?", but I don't think something small will look like anything other than a nice token as long as you haven't made any other love lorn gestures.
For example, second visit? Probably ok, even if she doesn't know you that well. She's probably not going to be completely taken aback or anything. Second visit following emails signed "love, Dave", daily texts, and snapchats of how much you miss her and have been thinking about her, complete with sad face? Probably not as much. I don't think there's ever a time that's "too soon", but then, I give people gifts on my birthday, so... lol
If you're going hot tub... one of you needs to bring the epsom salts, tea tree oil, and coconut oil to add in with the bubble bath. It's perfect after a romp! Leaves you feeling all loose and relaxed and ready to appreciate the new sheets and cuddle buddy 
Gifts are always appreciated.. Anyone who doesn't love gifts or ungrateful are Crappy human beings.... So anything you give her she will appreciate it!!! Wish more hobbyists were like you... My all time ATF gave me front row MADONNA tickets for Chicago & I adore him for that!!!
Good luck & keep being a gentleman!!!
...give her a break in between rounds. Shopping (you pay) should be reserved for more than a "regular."
I would be very careful about shopping. Shopping with a virtual stranger can be rather risky and can completely ruin the mood if she is overly mercenary and mistakes your kindness for weakness and heads right to the Versace store with your dick in one hand and your American Express Card in the other.
It's hard to have clear guidelines when shopping with a woman, you come across as a cheapskate if you set limits, which is the exact opposite of what you are trying to do, and you risk sticker shock if you don't set limits. So it's a bit of Russian roulette you are playing when taking a hooker shopping.
Forget the dollar menu and let her go for the Big Mac.
(I kid, of course. This being the Newbie Board I'd be remiss in not pointing that out.)
be sure you know what she likes. Many providers have wish lists or the like on their web sites that can guide you.
One more tip: don't give flowers unless you're sure she wants them. I know several providers who don't like gifts of flowers.
You can get a nice set for 10 bucks, 2 large and 3 small ones., at Walmart. I give them to each one I see, and never had anyone be disappointed.
LLAP,
Swim
Shopping might be a little over-the-top for me personally, but others would love it. If it's something you'd really enjoy doing, then I'd make sure you stress that to her.
Dinner is pretty much expected for an overnight, but I don't think you have to go all out for it. I'd expect to drop between $200-$400 depending on where you are, though.
As far as perfume, i wouldn't purchase perfume for her unless you know what she wears. Perfume is one of those things that can smell amazing in the bottle and turn to garbage once it's on. If she has an Amazon wish list, check that out and see if she's got perfume on the list. If she doesn't and you're still really into the idea of getting her perfume, ask her what she wears and what perfume she's almost out of.
the date starts after. It might include other entertainment. It is what ever the 2 of you agree. A lot of times it starts with a quickie, dinner, maybe entertainment, bed time romp, sometimes a 3 AM roll or not, an AM romp... breakfast. There should be adequate sleep time also & Shower time & understanding about private time.