Earlier this week, Wednesday secured the services of loan players Connor Wickham, Alessio Da Cruz, Jacob Murphy and Josh Windass for the remainder of the 2019-20 season, serving as a boost for the club in their hectic run of games this month.
Mindful that the Championship is likely to have a short turnaround before resuming next season in 2020-21, most likely in the first half of September, Monk says that striking fresh deals to keep those players would be advantageous - while recognising that it would not be straightforward.
Monk said: "I have really pleased with all of them. If the opportunity is there (to keep them), of course, I would.
"There's always an advantage with players who have worked with you and have a good idea of what you are doing and being in that environment, you gain time.
"Bringing a new player in, they have to settle and you have to see how they are in terms of how they settle into the group and the way you work.
"With a normal pre-season, that is not a problem. But trying to preempt what is very highly likely to be a short turnaround - having players you have worked with and can hit the ground running - if that opportunity is there, we will pursue that.
"But those conversations will come a little bit further down the line."
Wickham in particular has been an excellent impact upon the restart with two goals and Monk admits he would like to retain his services for next season, ideally.
He added: "If the opportunity was there, of course. But we have to cross those bridges when they come, right now we are focusing on the games which are coming thick and fast.
"As a manager, you have one eye on the future as well and you have those conversations with the club and we will see when those bridges are crossed.
"But of course, if there was a chance to bring back Connor, of course, I'd like to do that. But we have to see if that is a possibility, there are a lot of factors that go into that in terms of if we are capable or not."
Meanwhile, Monk says that club will assess the condition of defender Tom Lees, who missed the midweek game with West Brom through injury, ahead of potential involvement at Swansea City on Sunday lunch-time.
The former Leeds United centre-half was due to feature in place of Julian Borner, but missed out due to a hamstring niggle.
Scans have revealed no tear, but Monk says he will be guided by the player as to whether he will be involved at the Liberty Stadium.
Monk, who has Borner available again this weekend, said: "When we did the preparation (for midweek), he was starting, but two minutes into it, he felt something in his hamstring. We scanned him straightaway, but there was nothing and it came back clear.
"Really, we are dictated by Tom and how he feels. Tom will decide if he feels he can come back in. Clinically, there is nothing on the scan at all and we will be dictated by Tom."