Man, I can't count how many $s I've lost with expiring rewards points, but with a disciplined use of 1Password, so at least I know what accounts I have, plus a subscription to Awardwallet, hopefully this will be a thing of the past. Some notes, (by the way I was dumb, the old price as of February was$10/year, now it is $30/year, so it does cost something to keep track, otoh, you can lost$400 a year, so it probably does pay back).

1. It is a complete pain, but you can painstakingly go through Awardwallet and give it the codes to all your accounts. If you are paranoid, they have a client-side only option, so that all the passwords are kept on your local machine. This is like 1Password's system and is great.
2. For most of the hotel, airline and other rewards systems, it will periodically logon and tell you the expiration date and then you search the web to figure out how to prevent expiration.
3. It also has a "family" feature so you can keep the accounts of the family and each can access their own.

Last year, we lost a free ticket on Virgin, and who knows what else. Hopefully not this year.
As an example:

1. Alaska Airlines has a 18 month expiration policy. You just have to use their portal and you are OK.
2. Marriott has a similar rule and you can donate to charity 2500 points and keep it going.