K.W.
Sherrymore is probably Skerrymore, and Tullycolline is probably Tullycollive.
Skerrymore isn’t all that close to Longfield. It’s on the R 182 road from Castleblayney to Newtownhamilton. (A25 Blaney Rd in NI). When you cross the border into Co. Monaghan at county bridge, on that road, go about a quarter of a mile and Skerrymore is on the left hand side. A dead end lane leads south into the townland. At the other end of the townland there’s another dead end road leading north into it off the Mullaghduff Rd (which is in Armagh). At the time of Griffiths Valuation, there were 15 farms in the townland. I’d say they have been consolidated into two or three today, each accessed by the 2 lanes I have mentioned.
Tullycollive is closer to Longfield. Again right on the border, it’s about half a mile from Longfield.
You can see where the various townlands are, using this link:
http://www.logainm.ie
By William’s death in 1938, he was a labourer rather than a farmer, so their last house may not have been a farm, just a labourer’s cottage.
https://civilrecords.irishgenealogy.ie/churchrecords/images/deaths_returns/deaths_1938/04760/4275541.pdf
If you want to try and locate the various properties today, there’s a set of records called the Valuation Revision records, that run from the time of Griffiths Valuation in the mid 1800s up to about 1930. The records for Northern Ireland are on-line on the PRONI site but those for Co Monaghan and the Republic of Ireland generally are not on-line yet. However they are open to the public at the Valuation Office in Dublin. So it would be a question of looking each of these 3 townlands up in the 1920s, and if the family is listed, note the plot number. Then go to the maps attached to Griffiths Valuation and you should see where each plot was. Farms tend to stay put as you might expect, but if farms are combined some buildings may fall into disuse, so I can't guarantee the Gamble farm buildings are still standing. Many labourers cottages have been lost to progress over the years as few farmers need labourers these days and the buildings tended to either collapse or be swept away to create space.
https://www.valoff.ie/en/archive-research/
The Pollock pub may not be there any more, but I suspect their farm is. Since the family were still around in the 1970s, someone may know them. I knew a pub at Killead in Co Antrim in the 1980s that was a farm as well. It wasn’t very obvious that it was a pub. I am not sure it even had a sign. And when you went inside there was no bar. Just a room where folk met and drank. Your drink was brought to you mysteriously from behind the scenes. The Pollock pub might have been something like that.