We have the money it's not a matter of funds but rather frugality I'd say. He definitely wouldn't be grumpy about it. We've been talking about wanting to stay at Coronado, is it worth it if we won't be utilizing the pool etc? The other issue is I think he might be ordering a room decoration for V-Day does changing the room affect that?
I have no idea about the room decoration, so I wont speculate.
I think that on an anniversary trip, for $250, I would make the switch. CSR is stunning. WE never used the pool except to have coffee by or lunch, so pools would not factor into the decision. The resort itself is kind of Deluxe Lite, the amenities are more than a moderate, but not as pronounced as a deluxe.
We stayed there December 2015. The resort was gorgeous. The lobby was well staffed, and spotless. There was plenty of dining options right off the lobby, with a lounge and TS restaurant as well as CS.
The walk to to and from our room was different during the day from evening. The buildings and landscape reflect off of the lake during the day, but come evening, that lake shimmers. It is beautiful. The grounds impeccable groomed.
The rooms was clean, and we liked the wooden pocket doors that separated the vanity and clothes area from teh sleeping quarters. I wish all the moderates had this instead of a curtain. The beds were really comfortable as well.
I cannot speak to your budget, but I think that frugal is not a matter of not spending money, but being sure that money is well spent. My husband is frugal, as am I. We are not afraid to use money to enhance our experiences. If you change resorts, will you and your husband use any of the amenities? If not, your room is just the place you use to sleep and shower, keep what you have. If you will spend some time relaxing or dining at the resort, make the change.