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. 
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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