Windsor is definitely in a tough spot until Rychel makes some changes. Adding from outside the organization via trade isn't going to happen until they move bodies out and with their current draft pick situation they need to move DiPietro before that's a realistic option.
Currently Windsor's draft picks are as follows:
2019 - 4th, KIT 5th, KNG 6th, 8th, 9th, 10th, 13th, 14th
2020 - 4th, KIT 4th, OSH 4th, 7th, 8th, 9th, 10th, 11th, 12th, 13th OTT 14th, 15th
2021 - 4th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, BAR 15th, OTT 15th (Cond)
2022 - KNG 2nd, 3rd, 4th, 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, 15th
2023 - KIT 2nd, KIT 3rd, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, 15th
2024 - KNG 2nd, BAR 3rd. 4th, 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, 15th
2025 - KGN 2nd, 3rd, 4th, 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, 15th
2026 - 2nd, 3rd, 4th, 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, 15th
2027 - 2nd, KGN 2nd (Cond), 3rd, 4th, 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, 15th
2028 - 2nd, KGN 2nd (Cond), 3rd, 4th, 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, 14th, 15th
Doesn't leave Rychel a lot to work with in terms of bringing in outside players if he can only deal until 2024 (?). 3 2nds and 3 3rds to finish emptying the cupboards if he wants to add from outside.