Avoiding the Old Forest...?

[Inziladun]

Originally Posted by Tuor in Gondolin

Btw, a possible plot hole is the Bucklanders apparently
being totally unaware (unless I forget references in LOTR)
of Tom Bombadil, especially since he must have been not
infrequently in the eastern Shire rapping with Farmer Maggot
since I can't see Maggot's wife letting him traipse off to some
foreign place across the Brandywine.

Well, I don't know if Bombadil had set foot in the Shire within living memory of any of the Hobbits. His 'country' seems to have consisted only of the Forest and the Downs; and Gandalf (and Tom himself) stated he did not leave the bounds he had set for himself for any reason.
I think it more likely Maggot visited him, especially since Merry noted that he had been known to enter the Forest at one time.

[Rumil]

Tom seems to have had the odd Shire-wards excursion...

Maggot's sons bowed at the door, his daughters did their curtsy,
his wife brought tankards out for those that might be thirsty.
Songs they had and merry tales, the supping and the dancing;
Goodman Maggot there for all his belt was prancing,
Tom did a hornpipe when he was not quaffing,
daughters did the Springle-ring, goodwife did the laughing.

though admittedly he didn't get such a good reception at Grindwall..

'Hoy! Here's Woodman Tom with his billy-beard on!'
laughed all the little folk of Hays-end and Breredon.
'Ware, Tom! We'll shoot you dead with our bows and arrows!
We don't let Forest-folk nor bogies from the Barrows
cross over Brandywine by cockle-boat nor ferry'.
'Fie, little fatbellies! Don't ye make so merry!'

[Inziladun]

That would certainly seem to put ice on my theory, but I was drawing strictly from LOTR.