automation script

I need a script to do the following
(1)have a config file with the following for multiple servers: server hostname, username password, path in respective servers, branch to checkout, commands to execute(can be multiple)
(2)script should do the following:
(a)automatically login to servers sequentially
(b)go to specific path(default: home path), check for specific directory and enter into the specific directory
(c)git checkout the specific branch
(d)git pull
(e)execute command
if sudo access is needed in any command, which says something like this: "[sudo] password for", then input the password for that server for that user.
if any step fails, report in shell and exit
for every server it completes, it should ask the user for confirmation if its good to proceed for the next.
languages can be of (python or shell script) or any open source tool(usage of tools or libraries welcome, as that will take care of most of error scenarios, no need to reinvent the wheel)...suggestions welcome....budget: 10k INR

No freshers please, I am myself an expert in linux, so I wont consider any fresher like coding.