I played this game many years ago. Yes, I think the milkman comes, but you have to do some exploring first, and the timing has to be right. I remember little else, so maybe others will play along with you.
You really have to have everything. Put things in your pocket. When you've done pretty well everything, the game will tell you you need to go to sleep. Make sure to explore the dead American's rooms.
Make sure you have explored the American's apartment, smoked and refilled the pipe, read the diary, wear the belt, have the matches, have the torch, read the postcard, have the knife, have the three coins.
You can put things in your pocket. By now you should be sleepy. You will hear the milkman's keys jangling. Then meet him in the hall (he should not see or get into the room). SAY HELLO. Then you have some choices to make.
First you need to ensure that you buy the ticket to Dumfries, not Glasgow. In order to be able to do that you need to have decoded the book. To do that write out the alphabet, put the Code Hint (Julia) to correspond with the vowels; then fill in the rest). Once on the train get off at Crewe to get a newspaper. Then wait for the train to come to a complete stop and get off.