I felt a bit of context was missing from the programme or not fully discussed. One key element was that Harry had a perfectly decent relationship with the press when him, William and Kate were promoting their charitable work through the Royal Foundation, supporting the London Olympics or he was creating the Invictus games in the UK. He was positive, genial and fun. I think we all rather liked him then and the dynamics of the three of them. He wasn't displaying the animosity and sheer hatred of the press that he is now and he was willing to play the 'game' which I think the programme helpfully explained - you give the press some of what they want and they in turn give you an easy ride.
The problem was finding a girlfriend/wife. He wanted what his brother had with Kate, but he knew that it would be difficult for him to find. Firstly William and Kate had a lot off privacy afforded to them as students and so they were able to conduct a lot of the early years of the relationship in relative obscurity. But Harry knew that many women in their 20s or 30s at an older and more confident and independent stage of their life - not an impressionable 18 or 19 year old - would baulk at the pressures of having a relationship with him, being in the public eye, having to follow strict royal protocols and be followed by the press. Both Chelsey Davy and Cressida Bonas walked away from him because they weren't willing to take it on - it wasn't a life they wanted to lead. Honestly, who would want to live like that?
Ironically if he had looked more amongst his peers in the aristocracy he might have been more likely to find someone who was brought up with similar expectations on duty, stiff upper lip and traditional male/female roles. A traditional posh army wife would have been perfect. Of course they are rarer now than in his mothers day. Diana was a lamb to the slaughter because she was both from that background and an impressionable 19 year old and she was marrying a man in love with someone else.
But because Harry was more of a celebrity Prince (not army, hunting shooting, fishing landed aristo) he seemed to be attracted to more creative, feisty outgoing women who would find it particularly onerous and restrictive - not like Kate who was willing to hang about and wait for William (whilst he played the field) and to act the part of the dutiful unspeaking wife.
It might also have been that they very success of their tripartite engagement with good causes (Harry, William and Kate) made press and public interest even stronger, and the set up for a new partner all the more difficult.
There was an opportunity in the early days of their relationship and marriage that Harry and Meghan could have broken the mould a bit and modernised the royal family. That modernisation would have been held in check whilst the Queen is still alive but probably could have made more progress once she was departed. Instead by going away and cutting a new path they have forced William and Kate back into a very traditional and conservative role (though they were always more duty bound anyway).
Perhaps with Harry's personality it was always going to be a push for him to stay in the fold in the pointless role of the ever more distant spare to the heir.
But the key point for me that Amal Rajan made successfully in the programme was that once you take on the press and start suing them then its fair game for them to say what they like about you, without the deal with the press the coverage will inevitably be more challenging. There isn't anything more British than toppling statues and bringing back down to ground entitlement. There ain't anything much more entitled than a Prince and Duchess. Harry and Meghan don't have anything to lose now. But the Royal Family 'the firm' do. They need public support to continue and therefore however much they loathe it, they need a deal with the press.