The Possible Adventures of Young Bilbo

Tolkien had a section cut out of the Appendix of the Lord of the Rings that involved Gandalf telling, after the defeat of Sauron, the backstory of The Hobbit.  It was called The Quest for Erebor, and has been reprinted in various versions.  He explains that one of the reasons he chose Bilbo to assist in the quest was that the Shire needed to have someone to help them 'remember' - to get out of their complacency, due to the hard times that were coming.  When asked "Why Bilbo?", he mentioned that he needed someone from the most adventurous hobbit family - the Tooks - but with a more solid foundation, like the Baggins.  He remembered Bilbo from his youth, where he would pester Gandalf with questions, especially about those hobbits that went off exploring.
However, as the story proceeds, the whole scene from the beginning the The Hobbit, where Bilbo is flustered and put off by the appearance of the dwarves, comes into a different light.  Gandalf reveals that the dwarves thought Bilbo was a lazy, buffoonish idiot and only Gandalf's revelations of the map and key - and Gandalf making the declaration that Bilbo was a close friend and ally (something that the dwarves grudgingly could appreciate) allowed him to even continue.  He admits he had made a mistake, not realizing that Bilbo had become just as complacent as the rest of the Shire.
But is there more to the story?  Is there a deeper reason to pick Bilbo than just because he showed an interest in other hobbits that explored when he was young?
Gandalf mentions a terrible winter in the retelling, called the Long Winter - about 200 years before the events of The Hobbit - where he came to the Shire to help the hobbits.
"I began to have a warm place in my heart for them in the Long Winter, which none of you can remember.  They were very hard put to it then: one of the worst pinches they have been in, dying of cold, and starving in the dreadful dearth that followed.  But that was the time to see their courage, and their pity one for another.  It was by their pity as much as by their tough uncomplaining courage that they survived."
Bilbo, of course, wasn't alive during this time.  But there was another terrible winter years later - the Fell Winter, when Bilbo was 21.  White wolves invaded the Shire and the rivers all froze over; the following year, the meltwater caused massive floods.  In the text of the The Lord of the Rings, it is mentioned that Bilbo was probably 'the only living hobbit' to still remember the Fell Winter.
Now the Baggins family tree in the appendix to The Lord of the Rings has some interesting information.  The title is "Baggins of Hobbiton", indicating that the Baggins clan was associated with the village for some time; one would assume that most of Bilbo's relations lived in the area.  Even more interesting is that Bilbo has a great-uncle that died in Shire Reckoning (SR) 1311... and a great-uncle and great-aunt that died the following year.  Why is this significant?  Because these are the dates of the Fell Winter and massive flooding that followed.
Nothing is said of Gandalf helping the Shire this time around, but we know that the last time he visited the Shire before the events of The Hobbit wouldn't be for a few more years after this, so it is very plausible.  While probably not as devastating as the Long Winter, the surrounding land was ruined - the only other major human settlement in Eriador besides Bree, the town of Tharbad (southeast of the Shire) was abandoned due to the flooding. 
So, in a time of tragedy for the Baggins of Hobbiton, did the young Bilbo bravely step up?  Did he try to save his fellow hobbits from the cold, or the wolves or the flooding?  Did he witness the deaths of his family members?  I suspect that Gandalf may have seen first-hand the courage of young Bilbo in a time of crisis, and knew that he could rise again if the circumstances presented themselves.

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