Sherry, I trust you have read Rick's train tips, either in his books or on the main part of this website.
When I went to Cologne from Brussels (two nights in the Hilton) I bought my ticket online from the Belgian Rail website for something ridiculous, like 29 Euros - but I don't remember exactly. I printed out my bar-coded tickets before flying over there. No, you don't have to "validate" bar coded tickets that are not changeable and only good for one train. I forget if more than one conductor looked at my ticket, but there was only one ticket for each full trip. I told that story as a "travel time" tale, not a horror story of "Casablanca" flight from one country to the next! The conductors told me exactly what to do in person. However, the PA announcements might have been only in French, Dutch, and German.
The national rail sites vary from country to country whether you have to "click through" to an "International" page to price and buy International tickets. But all the countries I've been to sell International round trips that start and end in their country. You do need a few facts at hand, like which of the stations you want in a city that has more than one - or in Germany, which Frankfurt (like "am Main" you are going to.)
I don't want to tell you what is best for you, especially since you have so many short trips that might be cheaper as single tix, especially on weekends. But I have sometimes bought an adult (non-student) 10-trip ticket in Antwerp for a week of daytrips. (it's actually good for six months, but only to the station nearest the border if used for an international trip. And not good on Thalys) Anyway, this was to avoid waiting in line for a human agent, because the ticket machines don't work with Americano credit cards.
Another advantage of this 10-trip system is that you can write "Brussel" in even if you're planning to go only to Antwerp. Then if it starts raining, you go to the main Art museum in Brussels instead of getting off in Antwerp. (You can't write a destination in and get on a train that doesn't go in the proper direction for that city, though. You might get fined for that.) Note that Bruges-Gent is much less than one-tenth of a ten-trip ticket, at least after rush hour.
You might benefit from browsing the Trip Advisor Belgium Forum and reading some of the train questions that get answered there.
Edit: You might also want to Search or browse for comments suggesting that Bruges is very dull at night, compared to Gent or Antwerp. You will find no sign of "In Bruges."