Questions about traveling in January in Andalucia

I can't answer any of your specific questions but want to give you a heads-up about the need to get tickets ahead of time for the Alcazar and Cathedral in Seville. Those are two of the city's top sights, and their ticket lines (which are outdoors) can be very long. Buying tickets a bit in advance online will allow you to avoid a potentially long wait.

The difficulty with prebooking an on-going flight or a train to Seville on your arrival day is that you cannot be sure how long it will take you to clear Immigration, pick up luggage, etc. Your flight could run late or could even be canceled. Back in May I was 24 hours late getting to London because of a flight cancelation. On the other hand, last-minute purchase of tickets for Spanish express trains can be tricky, because those trains do sometimes sell out in advance. It would be really unfortunate to look at a schedule and see a long list of "Full Train" indicators stretching for hours.

It would be much better if you had multi-city airline tickets, into Seville and out of Madrid, but I know when I checked that possibility from my origin back in 2019, there was an extra cost of about $500. I ended up spending the first night in Madrid, but that's a really tough recommendation to make for a short trip like yours. Checking into a Madrid hotel twice would waste a lot of time.

I'm a little surprised, or more than a little, that the only train is at 1pm to Sevilla.

You could certainly have time either to fly or take the 1pm train, unless your inbound flight is drastically late.
You should have bought flights on one ticket from the US to MAD to SVQ, but I guess it's too late to change (??)
You do not have to call Iberia about taking medical supplies. You can take medical liquids in your checked bags or in your carry on, if they fit that.

In Sevilla you do not need a guided tour, or a "tapas tour." You can go on your own for tapas and on your own to tour the city.

You need to buy advance tix for certain attractions such as the Cathedral. Be sure to use the official online sellers.

I would discourage going to Ronda on a day trip. As it is, you have limited time in Sevilla. And there are 'white towns" that are closer if you really want to visit one. There are neighborhoods in Sevilla with white buildings--that's all a "white town" is..a town with Andalusia-style buildings that are painted or washed with white.

The major wine of the region--not the only one but the major one--is sherry. If you are interested in a sherry-tasting tour, I highly recommend contacting Shawn Hennessey, who is a degreed sherry educator and has lived in the city since 2019. (She comes from Canada) Her tours are fantastic and you'll get lots of food to go along with the wines. You can contact her at the link, below. I went on one of her tours last March and had a wonderful time! And great food and wine!!:

https://azahar-sevilla.com/sevilletapas/tapas-tours/sherry/

The province of Sevilla is not an oil center. The major oil areas of Andalucia are in Jaen province. And what would you see in an olive oil tour, unless you were there during harvest? Much cheaper for tasting would be to ask at a restaurant, or if you really want to do this, buy a few bottles of very good oil and taste in your hotel room, with bread.

A lot less expensive than booking a tour, especially with the size of your group.

For flamenco, the two venues I'd recommend are MUSEO DE FLAMENCO and CASA DE LA MEMORIA. Botha re small and you should book tickets online, again from the official sites. Get there early as seating is not reserved.

I'm happy to help with anything else....