I think I know my plan, assuming my Citi card does convert to AMEX. Note I already have the Surpass AMEX card, which offered me a free weekend night at my 1-year anniversary.
1. I am over 70% to my $10k anniversary night spend (which comes up in February). I think I can get there in the next three months, so I might as well keep the card until I get the certificate. Even with the second AF, it's like getting a room for $95 (regardless of the actual rate). I will have a total of two weekend nights in 2018 across both cards.
2. I will cancel the converted Citi card once it transfers to AMEX and find out what "options" they are offering to those with multiple cards.
3. I do think something will happen to HH benefits now that people can buy into Diamond. If things are diluted enough for Gold members, I will likely apply for Aspire, even though I have a high-AF card already in CSR.