The Hibs boss revealed he hopes to have up to four kids farmed out before the new season kicks off as he plans to work with a streamlined squad of no more than 24.
Booth spent the first half of the season on loan at Brechin City having been with Arbroath for the second half of the previous campaign, returning to Edinburgh in January and walking straight into SPL action.
As the 19-year-old established himself as a first-team regular, Scott Taggart forced his way into Calderwood's plans, featuring in the final three games having earlier been on loan with Ayr United.
Other youngsters such as Jordon Forster, Scott Smith, Danny Handling and Lewis Horner also made the squad towards the end of the season with Handling and Horner making their debuts.
Calderwood sees exposure to regular first-team football as the way forward for promising kids, particularly those too old to play at under-19 level but not yet ready for top-flight action and denied a regular game with the scrapping of the Reserve League.
He said: "I don't want the squad to be any more than 24. We want to have two, three or four out on loan almost guaranteed by the start of the season so that they are playing and can learn the game.
"We use the example of what happened to Callum Booth as a good example.
"If I have a squad of 24 with four out on loan and 20 training and available for the first team then that is almost where I want to be. Anything beyond 22 is too many because that is two teams."
Meanwhile, Calderwood has revealed he's closing in on a new striker, revealing he'd be "very excited" about Hibs chances next season if he were to get the players he's targeting.
Calderwood is resigned to losing Derek Riordan who is reported to have attracted a new offer from American club Houston Dynamo. The 28-year-old rebuffed an approach by the MLS outfit a few months ago but, as revealed by the Evening News, Dynamo haven't lost interest and are now said to have come up with a three-year deal.
On the prospect of new arrivals to join his first summer signing Ivan Sproule, Calderwood said: "We've obviously got to look at the forward line and the striker department. We hope to conclude and move forward on a striker shortly.
"I think that will make a big difference. In my mind's eye I know exactly the couple of players I want. If we get them then I will be very excited about our chances next year."