Jimmy,
My approach would be to check the connection from the BIG-IP command prompt with curl, e.g. curl -k https://10.10.10.10 and openssl e.g. openssl s_client -connect 10.10.10.10:443. See what gets returned by these commands.
I'd also look to run tcpdump/ssldump on the BIG-IP and narrow it down to the pool member and self IP of the vlan on the BIG-IP.
Finally, I'd check the following ASKf5 solution to ensure your health monitor complies to the correct formatting, especially the \r\n endings: Constructing HTTP requests for use with the HTTP or HTTPS application health monitor
Hope this helps,
N