I use commercial certificates on my Windows boxes for RDP I normally go for year long ones. I used to use the alpha certs issued from one of the various singlehop accounts on LET, these all appear to have been shutdown. 
Does anyone else know of a reputable free SSL cert provider, preferably year long.
I am tempted to look at lets encrypt, but think it’s going to be a reasonable amount of hassle!
I don’t mind paying if anyone uses a good low price provider.
Thanks!
Let’s Encrypt is fine, you just have to automate it
Yeah it’s automating the DNS txt record that would be the issue. These servers don’t run IIS or any form of web services.
I believe you can generate/renew the certificates in one machine and move them to the other, so you could setup a linux server/VM to generate/renew the certificates and transfer them to the Windows boxes.
You can indeed… however, you can’t point a domain at two IPs at the same time, so you would need to do some NAT magic. In all honesty I would rather pay £5 for a SSL cert for a year.