A one night visit to Gibraltar

We drove from Arriate, near Ronda, to Gibraltar arriving about the time you are planning. There was no line at customs or for the bus to the cable car. There was a short wait at the cable car. The only issue was, on that day, the buses then went on strike so we had a bit of a challenge getting back to the border. Would assume that you could take the bus to, or near, your hotel. Rather than stay at Gibraltar, we drove about 45 minutes to Tarifa which we thoroughly enjoyed.

Beware the monkeys at the top of the rock!! They are aggressive…bordering on dangerous.

I would always consider parking on the Spanish side and walk across the border. There is an underground car park within 5 minutes walk of the border which I've used with no problems. Be aware that the bays are quite small and if you have a large car it might be a struggle.

Thank you both for taking your time to respond. I really appreciate your help.

The walk from o'Callahan to the cable car is quite short.- 10 mins or so.
However, unless you particularly want to sleep over, you can see most of the Gib sights in one day.
You can also take a taxi tour from the Gib side of the border which goes to to top and stops at the main points on the way down.
There is a car park next to the cable car, but it is frequently full.
Parking in La Linea and walking the 400 yards to the border and a bus is a good idea.
It's the end of the day when the lines at the border can be long.
I think the macaques are great - just don't carry a plastic bag so they think you've got food.
The have learned to undo backpack zips, too.

Do you all recommend buying tickets for the cable car in advance? From what I’ve seen it is largely recommended, however I’ve also read that the cable car won’t go up if it’s raining or windy. Do they reimburse readily? I wouldn’t be able to stay a second night if this happens

I should just arrive. To the best of my knowledge, there is no "skip the line" for pre-purchased tickets. The major disruptor is several cruise ships arriving on the same day.