Hello,
This is exactly my job today: Delivery automation.
My principal customer is the French trains company (called SNCF).
I am the team leader of 10 persons (2 DBA's + 8 system administrators).
More than classic manual deployment, maintenance, incidents resolving, we do deployment automation because our customer wants to reduce costs and create a service center where people number is lesser, less expensive cost, simple actions to do that don't need experts.
So, with big trust on myself, i can tell you i am your man.
Why just 250$: because i have to catch projects on freelancer.com to get stars and good comments that will help me catch big projects (i am new here but i really have a big experience: i am 35 old man). So, just enjoy your chance because later (few months i hope) i will sureley be more expensive.
I saw your project video, it is really very simple compared to what i have done before.
I suggest you to make scripts on powershell for windows environment and shell script for linux.
Just contact me and i will give you more details if you need about my experience, automation features i already created before.
Good luck for your project.