We just happen to be lucky enough to afford to go out of pocket for meals.
Other trips we wouldn't be able to shell out $500 for meals out of pocket.
The frustration comes from the "let me check on that" attitude where the CM disappears from the check in desk for 30 minutes. That is a LONG TIME -- 3x.
So, just telling me to chill out and enjoy my vacation is difficult when I am locked out of my room at 9pm and have to tell the kids to color for an hour while I wait to get keys into the room. But thanks for the absolute lack of empathy for the situation and the "shut up and suck ot up" response.
Apparently, there is more to the story than you stated in your original post. From what I've heard, charging to the Dining Plans was not interrupted during the downtime. Charging to the room account may have, but everyone I talked to had no problems.
You said you have been paying out of pocket for two days. Assuming the day you posted (yesterday) as one day, you checked in on the 16th. Whatever issues you were having with your DDP from that day may not be related to the downtime. Anyone who was scheduled to check in on that day would have been pre-processed (similar to online check in). It may have been an issue with your reservation itself.
Did you book directly through Disney or through an outside company? If it was an outside company, it takes more time to solve an issue because it has to go directly through the wholesaler. It also would depend on which resort you are at. A few resorts were transitioning and had a longer downtime than expected.
I do agree 30 minutes and even an hour to wait is a long time. That person could have done things differently so you didn't have to wait quite as long. Unfortunately, that's something that can't be changed.
This process is a headache for everyone. Guest Relations, Central Reservations, Travel Agents, Front Desk, Concierge, Housekeeping, Wholesalers, Ticketing, and many more have to deal with these issues. I am certainty not telling you to shut up and suck it up. Trust me, know what you are dealing with. You shouldn't let this hinder your vacation, but you are letting it. Voice your concerns as necessary to a Front Desk manager and they should be able to help out with compensation. You will get reimbursed. It will get taken care of.