Why do esports organizations struggle to monetize their highly engaged fan bases?

Esports Organisations currently lack tools necessary to nurture its fan base to transition the relationship from non-transactional to Transactional and thereby longterm.

To precisely answer your question let us divide esports fans into 3 broad categories as per KBoom | Esports Fan App fanalytics:
1)Skill Based Fans
2)Entertainment based fans
3)Relationship Based Fans

Esports, unlike conventional sports has a big share of skill based fans. Live streams and twitter like-comment-repost contests can work well for relationship based fans. But, Skill based fans needs to be challenged to deeply engage with them. And hence the esports organisations constantly struggle to monetize their fan base. However, there are ideas and strategies that can help organisations engage with all the set of audiences. Division One Esports teams have started adopting quest based engagement strategies, and idea coined by Kboom Fanalytics in a recent blog post.