I will start with a partial response: consolidate the accounts whenever possible. That is the first thing you should do before going any further, in my opinion.

Combine your Hilton HHonors and your husband’s Hilton HHonors accounts into one joint account, as Hilton allows you to do this. You will then have 14,000 Hilton HHonors points with which to work towards an award.

Then, combine your husband’s two Continental OnePass accounts into one.