Many Thawte, VeriSign, Equifax, GeoTrust, and RapidSSL SSL website certs are being deprecated by Chrome from mid September. I recommend you check yours isn’t one of them. More details on my blog:
LetsEncrypt seems like a great choice if you have a VPS. It may not be an option on shared hosting though.
We provide the ability to get LE certs through DNSimple without needing to install an LE-capable server or management system locally. You do have to update the certificate every 90 days though.
We have automated renewals of our Let’s Encrypt certificates since last year.
Just one more thing not to worry about 
I think most of the shared hosting providers offer Lets Encrypt as an automatically renewed option now. Dreamhost has it as a free option through their control panel, and FutureQuest offers it as well. (I suppose not all the shared hosting providers have implemented it yet though.)
VPSs are at $5/mo. Maybe it is time to abandon the shared hosting?
I am in the process. Trying to set up Apache, the right version of PHP, import the SQL databases, set up sub-domains, set the certificates etc is pretty tedious though. I am planning to have another push on it this week…
If you don’t mind spending a few bucks, you can get all of that set up for under $100 on Upwork.
It is fairly key to my business, so I probably need to learn how to do it myself. Also I am wary about giving the passwords to my existing to server to a random person off Upwork.