29 nights in Spain and Portugal (Itinerary A or B)

You clearly like a fast pace, but a couple of red flags:
A:
If you have 2 nights in Sevilla and want a day trip to Cordoba, that is basically no time in Sevilla. I think if you distributed the San Sebastian nights among your trip, this plan would look better.
B:
If you have 3 nights in Madrid but plan three days trips, you do not have time for them all.

For Madrid I actually didn’t have much planned for city itself other than tennis event. Would try to combine Segovia and Salamanca for one day.

I am doubtful about combining Segovia and Salamanca on a single day unless you intend to have a rental car (meaning parking challenges and expenses in Madrid). Although there are a few trains a day between the two cities, there seems to be nothing in the middle of the day that would allow you to divide the time into two convenient chunks. I recommend digging into the rail schedule before making a final decision. I believe bus service would be too slow. In addition, from memory, both the train stations involved are a bit of a walk from key parts of the historic center, so there'd be travel time on foot as well as by train.

Travel time to and from San Sebastian will be substantial. Three nights there with a day trip to Bayonne will mean not much more than a day in the Basque Country. Will that be enough for you? I do like that area, but the pace of the proposed itinerary concerns me.

I'll echo the earlier comment that 2 nights in Seville with a day trip planned to Cordoba is not a good idea. You are planning to spend an equal amount of time going to Gibraltar. There's really no comparison. Do you have a personal reason for devoting time to Gibraltar?

Ronda is interesting and attractive enough that a lot of us have enjoyed seeing it--but certainly not at the cost of having only a few hours in Seville. Seville is not Rothenburg on the Tauber; it's 60 times the size of Rothenburg.

I know nothing about Benagil and have not been to Salema, but the word on this forum is that Salema has been spoiled by over-development in recent years. There are apparently better options on the Algarve. Transportation to that area from Seville will be by bus (I'd guess with a change in Faro), so this looks to me like a time-consumung transfer. It appears that bus service between Benagil and Salema is extremely slow. I haven't dug into bus-company websites, but I think traveling from Seville to Lisbon by way of those two places is going to cost you around ten hours; that's a painful amount of travel time for just two nights. I'd check to see whether there are flights between Seville and Lisbon.

Both are too much.
Also, 2 nights only in Seville is criminal.

I suggest skipping the Algarve in Portugal and focus on Lisbon and Porto (Douro Valley).
Also, skip Gibraltar

Yeah the more I think about it, the more I want to cut Gibraltar its out of the way and really just one day of sights. Sevilla to Lagos is about 4-5 hours by bus on rome2rio. I love the outdoors, the Algarve has the coastal rock formations and Benagil Caves but may have to be cut. I don't drink wine, would you still recommend the Douro Valley?

April 15 and April 24 are the first days of the tennis events in Barcelona and Madrid respectively, I guess I could have asked since the tennis events have locked me in a bit, does it make sense to just go from Barcelona to Madrid with no other home bases in between?

I adjusted option A, took night from Madrid to give to Basque. I could cut Lagos and give one of the 3 nights to Sevilla, no idea where to put the other 2 nights.

Arrive Wed 4/12 4n Barcelona (Barcelona Open Sat. April 15 - 23)
4n San Sebastian DT Bayonne,France
5n Madrid DT Toledo,Segovia,Salamanca (Madrid Open Mon. April 24- May 7)
2n Granada
2n Ronda
2n Sevilla DT Cordoba
3n Lagos (Bengali, Salema)
4n Lisbon (Sintra, Tomar?, {AM Obidos- PM Nazare(Sitio) combo?}]
3n Porto (DT Coimbra) Depart Thur 5/11

I adjusted option A, took night from Madrid to give to Basque. I could
cut Lagos and give one of the 3 nights to Sevilla, no idea where to
put the other 2 nights. Arrive Wed 4/12 4n Barcelona (Barcelona Open
Sat. April 15 - 23) 4n San Sebastian DT Bayonne,France 5n Madrid DT
Toledo,Segovia,Salamanca (Madrid Open Mon. April 24- May 7) 2n Granada
2n Ronda 2n Sevilla DT Cordoba 3n Lagos (Bengali, Salema) 4n Lisbon
(Sintra, Tomar?, {AM Obidos- PM Nazare(Sitio) combo?}] 3n Porto (DT
Coimbra) Depart Thur 5/11

Most would say put the extra nights in Sevilla.
If you decide to nix Algarve, I believe there is a bus from Sevilla to Lisbon that goes through Merida, which has some nice Roman ruins, if you find that of interest.
From San Sebastian, there is a great hike you can do along the coast from Zumaia to Deba, with interesting rock formations along the sea.
I'd be adding time in places not adding destinations, but we've been discussing Zaragoza on the Spain page, which is between Madrid and Barcelona and would make for an easy stop.
So when do you take the vacation from your vacation, lol? I do admire your stamina!

The bad thing about these long vacations is all the research and work that has to be done for them. If I was only going for a week it would be easy to just focus on Madrid and Barcelona. I just thought of moving Cordoba as a stop on way from Madrid to Granada and spending 2 or 3 nights in Granada and either 2 or 3 in Sevilla. My dates in Sevilla seem to overlap with the April fair 23rd-29th. Has anyone been? I'm concerned it will be too crowded.

You are right, that is because most would say two nights IS sufficient for Ronda and Granada (well, some are big Granada fans, but two nights is enough if you are going for the Alhambra). Sevilla has a much larger assortment of sights, you also want to do a day trip to Cordoba, and Sevilla just in general has many passionate fans. I also think interspersing some longer stays between the two night stays is important, but you know yourself better than we do.