More character spitballing...
OK, to work...
Sam Ripley was born to the Gilman family of Mass. in 1914. Orphaned under mysterious circumstances, the newborn was given to the closest relatives, the Ripleys, farmers in Kansas.
Whatever the reasons, the Gilman boys accepted Sam as a sibling. And Sam spent a generally happy (if somewhat dull) childhood on the farm. One of Sam's older cousins was a WWI vet turned crop duster and taught young Sam some flying lessons once he saw the young kid's enthusiasm.
As Sam approached adulthood, the young would-be pilot spent what little spending money was available on lessons and plane rental. Soon Sam took over the crop dusting and got a reputation as a part-time barnstormer.
After a few years, Sam was able to fly in Europe. Ripley made many friends and now worries about them with the worsening conditions and then the War.
And then with a new plane and crew, Sam planned a world crossing as a publicity stunt. The flight went well until some point and then no one really knows what happened next. Sam's plane was wrecked, the crew dead or missing, and Ripley suffered from sudden memory loss.
With no tangible evidence proving otherwise, the crash was assumed to be pilot error. Sam's pilot license was revoked and the shattered pilot was grounded and forgotten.
A year later, a near-bankrupt Sam was preparing to sell the plane for scrap when elderly Keziah Gilman, Sam's long-lost and unknown aunt, asked that Ripley take over the running the family's colonial-era inn.
With nothing better to do, Sam has taken over the running of the inn. In a desparate attempt to increase revenue for the tavern, Sam has taken what weird books, statuettes, and various arcana from the attic as decoration for the newly-christened Witching Hour Bar in the inn.
At this time, Ripley is resigned to being grounded for life, physically and mentally damaged.
Notes and Options:
As has been mentioned before, Sam could easily be short for Samantha. Having grown up with about five or six brothers, she would be a natural tomboy and rarely calculatingly feminine.
Sam's family connections to Lovecraft country may be nothing more than a plot device to explain why Sam is in Arkham. Or it may hint at a tainted bloodline if that serves David's purposes. Should an unearthly legacy appeal to David, Sam will most likely have some uncommon mental or physical distinctions (in addition to strange dreams and a facility for inhuman phenomes).
Even with a completely Euclidian genetic code, just not being completely WASP might be considered 'tainted' blood. I will assume that Sam is of mixed ethicities but tends to resemble a WASP father. It takes a little getting to know Sam to find out otherwise. That way, this is as much or as little a part of the game as David wishes.
By being 'passably' WASP, this means Sam may have to work at keeping this secret (which could be a red herring for others if the GM needs it). It could also be that Sam is illegitimate, a big deal for the time.
I have changed the USAAF origin to a civilian origin. The reason being is that a bomber pilot doesn't have much plot potential until the war starts for America (and I don't think it has yet when the game starts). 1941 was still the age of heroic aviators, Earhardt, Lindburgh, etc. It would also allow a more realistic origin for Samantha who couldn't have joined the military as Samuel could.
One of the theories surrounding Amelia Earhardt's disappearance is that she was actually on a covert mission to survey Japanese military strength under the cover of a navigation error. It was (according to the theory) believed that the Japanese would not kill a woman prisoner (or course, this would have turned out to be literally dead wrong). Samuel or Samantha, a covert mission would make Sam become important to the US government and maybe known to the soon-to-be Axis governments. This might have had something to do with Sam's final flight.
So,what was Sam's final flight? Short answer: Whatever David wants it to be. At the very least, it throws into question Sam's competence and sanity (which is perfect for a Lovecraft story). Here's a mundane explanation, a very powerful storm damn near crashed the plane, Sam suffered head trauma and can't remember that this was an ordinary but tragic risk of flying. Sam's adopted last name of Ripley is a tribute to the Alien movies (which are themselves a tribute to Lovecraft), as Ripley is another pilot who was grounded after not being able to prove fighting a monster.
Now, Sam runs the Witching Hour with the perfect mix of doubt and dread. Who knows what powerful artifacts might be on the wall as decoration? And, of course, this is only if David would prefer Sam in charge of the bar.
I welcome any comments, question, or suggestions. Either way, I will keep refining the character until game start...
Gerry