(1) After my property tax got lost in the mail one year, resulting in a late fee that upset me a lot, I have instead chosen to pay it online, in a lump sum for the year as soon as I know how much it will be. To avoid the credit card or debit card fee, I just have the exact specified amount deducted straight from my checking account at a cost to me of $0.00 (a savings of $0.49, I suppose). It is deducted promptly and that is that.
(2) I don't subsidize Hallmark. I do respond to Christmas cards by sending a long, newsy e-mail with attached photos in return. More effort but a lot more personal, and they usually initiate a number of e-mail exchanges back and forth as a result.
(3) Last year I had one important correspondence (concerning an investment) that needed to be sent by mail so that they would have my signature on file. So there's ONE stamp.....
I am obviously not nearly as important as you are because I just don't have to send certified mail every time I turn around (and fewer and fewer of them seem necessary as the years go by).
(4) Flood insurance needs to be sent in by surface mail instead of snail mail, IIRC, although I believe they have changed that or are changing it soon. But, I am still sending it by snail mail. So there's another stamp (unless I used a pre-paid envelope).
Not sure what I used the other 5 stamps for.
I have paid all of my other bills electronically since the year 2000, by automatic deduction from my checking account, with no errors; the accumulated postage that I have saved would be enough to pay for a considerable error after all these years, but still no errors.
I keep in touch with people through e-mail, not letters, since everyone I know is quite capable of handling e-mail.