All other things being equal, use a web hosting service like NameCheap or Hostgator that provide a free SSL certificate for every site that you host with them. That is a key thing – every – as many hosts say they provide it, but only for the primary site and not additional sites.
A good example of that is Hostinger who are wonderful in many ways, but only one of your unlimited websites has the SSL. They provide instructions on how to add free SSL to the other sites, but it takes effort, and you need to repeat that effort every 2 months.
Note – it is common for the free SSL to not automatically start running. Typically asking support to do so, over online chat, takes just a few minutes.
Hosts that have free, automatically enabled SSL for every site
- Namecheap
- Hostgator
- Hostinger (recent feature – instructions here)
Free SSL that you install yourself
It is provided by Let’s Encrypt, a non-profit providing SSLs for 300 million websites. The implementation is not too difficult, but it is a bit tedious. Multiply that by however many websites you have, and doing it every 60 days, and then you have to consider how much your time is worth.
ZeroSSL is similar and seems a bit easier
BuyPass are similar, except their free security certificates last six months.
Automating renewals for both is possible with a tool called ACME, but requires a lot more upfront effort and technical expertise, and might vary according to your hosting service.
Paid SSL
The cheapest I have found is Comodo PositiveSSL at ssls.com, which is $8/yr but discounted for multiple years.