This! When I was on a cheap shared and hosted solution the idea of LE was waaayyy above me.
But, I moved over everything to AWS, for the same amount of money (OK, ~$0.60 more than what I was paying before - relatively nothing), and it became a piece of cake.
That initial time commitment to the move, though, will never be recouped. I do however look at it as a career-expanding experience (fairly confident in how AWS works for projects/companies), so I got that going for it.
But, I moved over everything to AWS, for the same amount of money (OK, ~$0.60 more than what I was paying before - relatively nothing), and it became a piece of cake.
That initial time commitment to the move, though, will never be recouped. I do however look at it as a career-expanding experience (fairly confident in how AWS works for projects/companies), so I got that going for it.