Hi, first post--I don't see a general hotel miles/points board topic, only specific hotels/chains. The credit card boards deal with airlines, status, tiers, luxury hotels, etc--which don't apply to my specific goal. If someone could suggest a topic home, that would be great!

We are retiring in a couple of years and want to spend three months each winter at a different ski resort. VRBO/Airbnbs aren't that great of a deal at the moment, and RV's have issues in the winter. I am thinking that we choose the resort 18 months in advance and get a credit card that targets one or two of the hotels there (Holiday Inn Express/Fairfield Inn-ish). We have a 5K a month credit card spend.

I'd like the most free nights possible, and we don't mind moving rooms as needed. We could also be maximizing the "stay 4 nights get the 5th night free" type deals. At some point each winter we get VRBO/Airbnb's which become affordable because of the savings from the free hotel nights.

Are there any other strategies I should add to this plan? Thanks again for pointing me to the proper place to read up.