What I encounter when running a droplet on Digital Ocean ($5 account) is when you deploy an update it can sometimes take a very long time to finish… I have had deploy-times of more than an hour. :-S
I figured out that before you do a deployment, go to your target settings and in the docker machines panel, restart the machine.
After the droplet has been restarted the deployment time is almost as fast as on localhost. 
Haven't seen that before. It does take some time on the build context step, but that is also random.
Not sure restarting the machine is a good idea. Maybe you need to check the deployment settings. Make sure your user uploads folder is in gitignore.
Oh yeah, I should mention that I do that on my live test server 
Wouldn’t probably do that on a live production droplet, although if the downtime can be reduced this way …
I’ll check my gitignore setting again… thanks