Can Mr. 篠原 deliver on his Christmas promises in time?

(Names and titles have been changed in order to have the moderators not construe this question as a “self promotion”)

In this alternate history novel I have planned (title withheld for above reason), for the 1900 Christmas Season, he will give everybody in Nebraska five presents worth up to $1,000 each.

(He does start out with $(((2^45)-1)/100) so he can afford it. I dare you to decipher that amount! Can you do it?)

However, he will only deliver the presents in his “Santa 篠原” campaign to anyone who writes him a letter.

Moreover, even though he won’t give raw cash, he will pay off people’s debts up to $1,000 per “present.”

But for this to happen on time, how early must he start his “Santa 篠原” campaign?

Also, without FedEx and UPS around in those days, how does he deliver these presents in the fastest times possible?

Moreover, even entire houses used to cost less than $5,000. How many people would he need to hire on as construction crew, per house, in order to construct 1,000 square feet a day?

(I understand that houses may not be finished in time for December 25, 1900, and I’m sure the present recipients will understand. But making the promise of building a house does count, does it?)

Lastly, any other logistical and other steadfast issues in this gift-giving campaign that no amount of money can rectify?