I’m pretty new to wearing tail plugs myself
That said, as I understand it your questions will have different answers depending on the tail and depending on the person. I for one enjoy wearing mine for hours and hours, though I don’t wear it in public because I don’t see any good way to do so and still be able to sit in a 100% sanitary way. For play parties though… well, I haven’t worn mine to one yet, but I plan to at my next one! I like to sleep with mine in too, and it didn’t take me long to get acclimated enough to manage that (though to be fair I seem to be naturally relaxed with anal play, your mileage may therefore vary). A tail with no structure to it (some have wire or other stiffeners to make the tail stand out rather than hang free, but that’s the minority as I understand it) may swish back and forth a little when you walk, which I enjoy, but that depends in part on the weight and length of the tail, as well as your gait.
Really all of this depends on what tail you get and what you want your experience to be like. If you want to be someone who wears their tailplug whenever possible, every day, go for it! If you want it to be a “sometimes snack”, well, that’s good too. So long as it’s well-constructed and is a good size/shape for what your ass can handle, then you should be able to enjoy it pretty well.
Any more specific questions? Feel free to PM me also if you want to have a more in-depth conversation about this.