Sadras
Legend
3.) Everything below her waist automatically falls off on the ground. Any armor worn on her legs, boots or shoes, and pants ends up on a pile on the floor. Its probably more "realistic" than trying to explain how her gear merges into her, but everytime she shifts back; she's naked from the waist down. (I suppose a robe or dress would still work though).
4.) As 3, but unless she takes the time to take off said items, they could be ruined. (Clothes ripped, buckles break, shoes tatter). Most "realistic" type of transformation, but least "fun".
So I'm looking for some advice on how to handle this transformation in the most logical (yet fair) way.
We have a werebear in our group. He is a druid, a rather large man.
For being a werebear he gets many benefits - advantage on perception checks (smell), higher strength score (which includes carrying and lifting as we play encumbrance), ability to climb better, incredible regeneration rate (a little different than complete immunity), and the ability to transform into bear and hybrid form.
The following are his disadvantages - shapechange destroys restrictive clothing worn (so he wears a loose pants and no armour), animals generally shy away or are fearful as they pick up his lycanthropic nature, he eats double the quantity of food a normal person would (given his size and lycanthropic nature - explaining it has an accelerated metabolism)
So considering your options, I would definitely say number 4, unless she wears looser clothing then 3 is also an option. For instance a dress with sandals/light boots - you could say the transformation pulls the foot up before joining to the other and then extends to form a tail. Legging/pants would have to be taken off, destroyed and/or do physical damage to her when transforming.