I think you are vastly overestimating Harry’s worth.
Diana got £17 million in her divorce -a year later she was dead but hadn’t changed her will after she got the settlement. The £17 million was reduced to £10 million after IHT.
That was split between them.
If £5 million was invested until March 2020 without drawing anything from it and assuming a mid range 7% annual return (neither ‘safe’ or ‘reckless’) remembering we had a bank crash in 2009(? Or was it 8?) it would be worth £20.4 million by 2020. So not several tens of millions.
The Queen Mothers trust had quite a few beneficiaries -her estate was mainly made up of jewellry &a Monet -so the capital she had put in wasn’t huge -she famously had an overdraft which was paid off by her daughter every year,
He will (IMHO) have been worth maybe £30 million. Nothing really in the circles he rubbed shoulders in, but because he had never had to (or would have had to) worry about a home, or bills (his dad paid everything from the Duchy of Cornwall) and he got an allowance why would he worry what he was actually worth? The pot was always there and he thought it always would be,
If he and his wife had been more amenable and less jealous they would have been living in apartment 1 in KP with a nice place in the country for weekends. All bills, staff, travel, clothes for work, school fees for children would have been paid by duchy of Cornwall then Lancaster, HIS money would have paid for cars, holidays etc - but he would still likely have got an allowance for ‘spends’.
He never eve4 anticipated or had been brought up to worry about money.
Just like he wasn’t bothered by living in Nottingham Cottage.
It wasn’t till he met Meghan who was quite happy to tell him how hard done by he was that things went Pete Tong.
They had to get a large mortgage on Montecito house so one can only assume the same would be applied to his house here, I very much doubt he’s got £14million available to buy a house outright - the Montecito years have been hellishly expensive and running that house,staff, travel, security, taxes on earnings and and and will have sucked dry anything he got from ‘Spare’ and whatever Netflix/Spotify actually paid them for the (very little) output.
He’s not ‘skint’ by normal standards but by Meghans expectations he’s dirt poor.