@Katalanta
You bring up some good points, and IMHO, and I could be very wrong about this, but I feel it is generally easier for a woman to meet men than it is for men to meet woman. So if you are concerned about scaring a prospective male off, think how it feels for the poor males that have a much harder time hooking up with females.
Outside of that I think you have to kind of sort the people into roughly 3 piles and perhaps treat them a bit differently.
I would classify the piles as..
1) Prospective life mates. These are people you really click with and you would like to be in a long term relationship with. This pile needs to be treated the most gingerly IMHO. Different people are into their kinks by different amounts. I could not imagine a long term relationship without my kink. So, when I was in the looking for a life mate mode, I would get "traditionally" kinky fairley fast, but also go out of my way to make it enjoyable. Toying with her ass while eating her out as a prelude to anal, getting insertion toys as a prelude to speculums. And used the results of that type of activity to judge if we were really sexually compatible. Some people may not require that degree of sexual compatibility, but I really do. If they responded favorably, I would ramp it up and soon med fet was not that big an incremental jump. By that time, many of my old GF's were pretty excited at the prospect of being eaten for hours and funked really well on my exam table. If they did not respond well I would generally give the lower level stuff consistent tries and more often than not they would just go away on their own. No big low up etc etc. They would realize that we were not compatible and fade into the background. One thing with a prospective life mate, it is a lot easier to be open about our fetish early on as opposed to later on. I also always ask what she likes and try to get her to open up and tell me what she *really* wants.
2) 1 nighters or quickies where you definitely want to get fucked. Stick to mildy normally kinky the first round, if that freaks her out, throttle it back. Get both of your rocks off, and don't go back there again unless you are so hard up you want boring sex.
3) 1 nighters or quickies where you really don't care. I have been known to crack out the speculum. I mean I try and warm them up to the idea of insertions etc first. I have been called a perv other things. I have also had some fun times. Much like a life partner, I try and find out what she really wants. And not the vanella shit on the surface.