Sue I think if you arrive at the hotel just before midnight, it would be to your advantage to go that route
and book that day.
Your room would be held for you even if you did not arrive until just after midnight.
You could check in and go straight to your room.
One year I arrived at HR at 6:00 am.
Room not ready until 4:00 that day.
Never booked the first early morning flight after that.
I would not mind booking a flight that landed in the evening.
I would know once I checked in, my room would be ready for me.
This year I did third flight out to get to Atlanta.
Second leg of flight, had me arrive about 10:30 am to the hotel.
Will avoid that time frame next year as my room was not available until 3:00.
But when I went, hotel was only booking not even 50% of the rooms due to covid situation.
Rooms sit one or two days after a person checks out before it is cleaned.
You are planning your trip for later in the year and hotels may readjust and have more staff when you go.
and book that day.
Your room would be held for you even if you did not arrive until just after midnight.
You could check in and go straight to your room.
One year I arrived at HR at 6:00 am.
Room not ready until 4:00 that day.
Never booked the first early morning flight after that.
I would not mind booking a flight that landed in the evening.
I would know once I checked in, my room would be ready for me.
This year I did third flight out to get to Atlanta.
Second leg of flight, had me arrive about 10:30 am to the hotel.
Will avoid that time frame next year as my room was not available until 3:00.
But when I went, hotel was only booking not even 50% of the rooms due to covid situation.
Rooms sit one or two days after a person checks out before it is cleaned.
You are planning your trip for later in the year and hotels may readjust and have more staff when you go.