My husband and I are feeling incredibly stuck when it comes to making a decision on where to move next, and would value any advice or opinions from outsiders at this point. 

Background: I’m 31F (American) and he’s 43M (South African). For the past 10 years we’ve lived abroad in Botswana. I work remotely for a US-based company and he’s a shareholder of a small company based here in Bots (but he can transition to remote work).

We are considering moving to Spain (a little town outside of San Sebastian). We are also considering having a baby in the next year or two. My parents (retired Americans) now live in Spain and we really loved it there in the times we visited. We are considering Spain for these reasons:

1. Crime is low in my parents’ town and it seems like a really safe and wonderful place for a potential child to grow up (plus after being in Africa so long I want the safety for myself/my husband, too).
2. The area we would live would offer huge lifestyle improvements and access to things we don’t have now and desperately long for (culture, variety of food, live music, different activities and sports we can partake in, access to nature we don’t have anywhere around here, things we desperately miss and long for after being in Bots for so long).
3. We’re excited to explore Europe and have residency there, which is a huge benefit for my husband who has a passport that generally makes it very difficult to travel outside of Africa
4. My parents would be very hands-on grandparents and that would be a benefit, even if we couldn’t necessarily afford nannies (yes, I know these two things aren't the same, but it's still a plus).

But we also have major hesitations, due to the following:

1. There is no tax agreement between Bots and Spain, so my husband will need to pay double taxes. Ouch. This would make our combined income, after taxes and monthly social security payments, about 70,000 Euros (maybe more, but we want to be very cautious with estimates). Right now we manage to save a solid amount of money every month and money genuinely is not a stress in our lives. We're scared of moving somewhere where it would become a stress or we wouldn't be able to save.
2. Our Spanish is conversational at best. We speak Portuguese but are very worried about the language barrier, even though we would start language lessons immediately 
3. We’re worried about assimilating and making friends (my husband more so than me)
4. We don’t know what the medical system is like (how easy is it to find doctors, make appointments, etc?). We like that in South Africa you can book an appointment with a doctor directly (no referral needed) and get very good medical care for very cheap.

The other option is that we go to South Africa. The benefits here are:

1. Everyone speaks English
2. We have health insurance in SA and the private medical system there is very very good 
3. Cost of living is still very reasonable/affordable (this could also be true for Spain but we haven’t spent enough time there to know for sure)
4. My husband is South African so the process of moving there would be fairly easy and I would qualify for a spousal or remote worker visa.
5. Childcare is incredibly affordable. We could have a daily nanny if we wanted to. 
6. We already have a car in Bots so bringing it to SA means we don’t need to buy a brand new car
7. It’s easier to move our cat to SA than it is to Spain (30 hours of flying and driving for an anxious cat is a terrifying thought). 

Downsides are:

1. The crime in South Africa is awful. I hate the culture of everything being behind bars, walls, and electric fences. When we go visit SA I get so sick of the constant vigilance. I’m hugely independent - hiker, climber, outdoors person - and that would be taken from me in SA because women can’t do anything on their own. My head would always be on a swivel. 
2. Husband would still have to pay more in taxes because he currently avoids it by living and working in Bots. Moving to SA means he will have to pay taxes there which are considerable - and you don't get any benefits from paying taxes in SA.
3. Rent seems to be about the same in SA vs. San Sebastian, although in SA you get more space for what you pay.
4. I honestly always said I never wanted to live in SA. The infrastructure is falling apart, the culture of everything being in a shopping mall, the pollution and trash… I just think after so long in this part of the world I’m sick of it. Husband agrees. The only place I would actually consider living in SA are Cape Town/Cape Winelands but my husband’s family and friends are in KZN so that’s where we would probably have to live.

So this is where we are. If anyone has moved to either country with similar feelings or in a similar situation, or honestly even if you just are bored and feel like weighing in on a stranger’s life haha, please, I’m all ears. 

Thanks, folks.