We've talked with Lyn on several occasions, she is a very sweet lady. The first time we had a conversation, we were sitting right next to her and she instigated it with a small comment. Very normal, just as one would have a conversation with any stranger you see for an extended period (e.g. ride lines, on a bus, in a theater, resort lobby). She does have a lot of dolls and stuffed animals with her, in a rolling suitcase - not spread out on the benches or anything, for posters who are wondering.
We have often seen GF cast members talking with her, laughing, holding her hand or generally making her seem welcome. A couple of CMs have told us they sometimes spend their break time with her. I have no empirical proof (as if I would want any!) that she is welcomed
by management, but if they simply tolerated her, I think they would instruct the CMs not to encourage her. Just my opinion, of course.
The loitering comment is kind of out of left field, as all the WDW resorts are open to the public.
None have any rules that make sitting and enjoying the lobby area off limits, everyone is free to come and go as they please.
OP, I didn't find your first post strange or stalker-like!
I thought it was perfectly apparent you had met and talked with her in the past, and wanted to know if she was still there so you could chat with her again. Quite natural to ask on the DIS, where many posters have just returned from WDW.