I don't usually make recommendations for things like this, but since this post is semi private among your friends and not in an open group or whatever. here you go. I'm a HUGE fan of WPEngine. Costs a few bucks more than most of the others on your list - but the SSL is free (and once installed, it automatically updates when it expires) and installed with a few clicks - no code pasting. CDN is free, too (basically your cloudflare situation is part of it). The best part is the support. I've used them for 25+ clients for the past 5 years or so and have exactly ZERO complaints about support - not something I can so for any other service I've ever had. Staff is knowledgeable and, unlike most support teams, they have NEVER said, "It's the plugin's fault -contact them" or "It's Wordpress's Fault - contact them" or "It's your fault - fix it yoruself". They have always helped me actually find the problem. In the few cases where it actually WAS the plugin's fault (usually, I can diagnose that before I contact hosting support) - they helped me at least get the site working well enough that we could do business while I dealt with the plugin people. They're all just. good. Any client we've had for the 5 years we've been using them has had at least one server hardware upgrade, too. A few have just recently gotten their second one. So you know you're not on an ancient, overtaxed machine. They have TONS of security and server stability things going too. No need for a caching plugin - it's handled much more efficiently at the server level. I've never had a site hacked on there (knock wood) which is something I can't say about most other hosts. So. while, on the surface it looks like you're paying a bit more, you're not really. The things that are added on are good choices too. (Not stupid things to drive the price up, but good common sense things you'd consider adding on yourself). They bought FlyWheel recently, too - which means you can now set up a local install for development and push your changes right to the site. Very cool.