Superb write-up & notes from N.Gauthier & ties up with what limited I know.
Now, in answer to the 'original poster', this, but compiled with observations of my own, as both a local resident & a few indirect links.
"...Would the Lady give SO much many, to so many people & yet..."
From what I know, it's well-known round these parts (Snettisham, Heacham & Hunstanton), that one or more of the Rolfe Mother's were generous beyond measure, as many local schools & buildings & poor folk, were well financially bestowed by the Rolfe's, hence as to "Why" the family were held in such high regard by the locals.
I did know some facts, many years ago now, but as with all of us, age & advancing years DO take their toll on the memory, plus, most of my historical interest, is taken-up by WW.II Military history & even those huge memory-banks often fail, even after something that I've studied in-depth & then moved-on, yet, needed to recall 15+ years later.
My own Dad's Dad (Grandad), was born & bred in Heacham, plus, my kids also went to school there & my wife played keyboards & done an address there, inside St.Mary's, at Easter 2004.
I live nearby & use & go thru Heacham all the time, plus, most importantly, no-less than 27 of my own family are buried there, in the Churchyard of St.Mary's itself.
When I went looking for Edward & Margaret's gravestone (my 2 x Gt.Gramp's), I walked inside the Rolfe's own plot.
They were so (naturally) affluent, that they have their very own (large), secluded churchyard plot-area, although I've not walked-in there since circa 2004-2005, despite it's only a few miles from where I'm typing this.
With some strange wierd (unplanned), irony, my Paternal Heacham Grandad worked for L.N.E.R (at nearby Lynn) & soon became a Steam-Engine fireman, then, by 1935, a Steam-Train-Driver & settled in London, which is why I have a strong London accent, despite my own family tree (Paternal-side), originating from Hunstanton, Heacham, Sedgeford & Docking (all neigbouring local villages, as used by the Rolfe's themselves - When Pochohontas & John Rolfe came/returned back to England for the 2nd time, she fell ill, died on board ship (along the River Thames), & with some degree of irony, was buried at Gravesend in Kent, on the exact opposite side of the River Thames from where I was born & bred & raised. It wasn't until I was in my late 30's, that I even knew or realised that she (Pocohontas) had died & was buried more or less opposite me & yet, her own husband (John Rolfe), had been born & raised in amongst my own folks & family in the village of Heacham**
Seven of my Grandad's siblings were also born/raised there, plus, my family owned a farm at Heacham, of which, before my family took charge, the Rolfe's would have known & maybe even traded there...
(or even could or may have owned themselves)
So, to the original poster, yeah, it's ENTIRELY possible that the super-generous Rolfe's female forebears may well have splashed-out on the locals with extreme generousity, whilst ignoring those going what we nowadys call 'stateside', as, remember, once the colony had finally settled & (tried), smoothing things over with the Powahtans (after many decades), the Tobacco growng industry quite literally took-off, due to super-high demand of Tobacco in the U.K. & the rest of Europe.