With MoreSpeech I wonder if there is a sense of being overwhelmed by too much choice. 6 in the first screen, then under each there is another 10 to 40ish choices. I'd bet if you took away the "risk of making a bad choice" from the user they would feel more comfortable exploring the app and sticking with it. A design that focuses on Gamification and unlocking the next exercise instead of showing all exercises at once might reduce the problem. On the landing page you show Achievements and work in the psychology of collecting those markers and the stickiness might go up.
Ask yourself why the user opens the app the first time, the sixth time, the 20th time. Likely what the user wants to see for each of those is different. The First time is an obvious place to put a quick UI tutorial, ask some probing questions to setup their flow through the exercises (prioritized based on symptoms?), the sixth time you are probably introducing the last (prioritized as least important) top level category with a tutorial on how to "play/complete" the exercises in this category. On the 20th launch the user might be coming to their scoreboard with a big button that say "continue exercises" and the app picks the next "appropriate" lesson. They feel good to see that they're 23% complete, and have 7 hours of therapy this week under their belt. A lesser button on the dashboard might be to "repeat exercise" which shows the more complex UI that is the app today so the user can go back and try again, improve score, etc.
Questions I'd want to know before I'd start doing 1:1 tutorials:
How long does typical therapy last (duration in months X price/m)? can you afford to do 1:1 and still be profitable?
Is the Purchaser always the person under therapy? As a son-in-law to a boomer who has had a stroke I might buy the app for my father-in-law (and the iPad to run it). And my wife might be enforcing (encouraging) its daily use in the beginning of therapy. Are there features in there for Me and My Wife? Can she see/monitor his progress and participation? (my wife is doing your 1:1 tutorial for free)
It looks like a great app and awesome content within. At the very least I'd kill the free trial and go with limited demo. Keeping 99% of the content behind the paywall. (Option #1)
Yes, do the Live Webinars and then afterward replaying the recordings makes more sense to me than 1:1 hand holding (option#2), employ a Drip strategy to educate people who give you their email (signups in paid and demo category). Sending out links to upcoming webinars, or past recordings.
Option #3 is much like the features I imagined for my wife above. I'd be careful building more features ahead of talking to customers. Talk to therapists and children of patients before doing any coding. This is really about lighting up new marketing channels.
An Option #4: affiliate program where the therapist earns a portion (say 20%) of the monthly subscription and has their dashboard view of all their patients, thus enlisting them into the sales process. (give each therapist a "coupon code" to track their patients' signups) Again, talk to therapists before building this thing. Get their commitment before doing the work. Note: running Affiliate Programs tend to invalidate your merchant account agreements. Check into that too.
(please forgive many of my assumptions if I've missed something, I've gleaned the nature of the UI from the YouTube vids)
EDIT: It occurs to me we have a blind spot based on the phrasing of the questions. Instead of Free to Therapists, introduce a "Practice" License that a Therapist Office can buy for say $15000/yr and all their patients get the Service for Free under that license. This changes all of your support struggles and make 1:1 part of the sale. At that price they could expect onsite training.