Redmine

I currently run a redmine server for myself and a friend.

I have always found the time tracking clunky, and currently buggy for the version I am using (for example in worktime daily report, if I click the "+" to the right of an issue, instead of adding another new line entry, it take me up to the top of the page and nothing else happens).

So I have been looking at some of the shiny time management software like "wrike, asana, click up etc". Having tried clickup for a week, I am missing redmine.

When researching redmine I read:
"_Some of the main features of Redmine are:
...
Time tracking_"

This really surprised me. When I uses the time tracking module, it was a plug in from what seemed like a Japanese humanitarian guy, and it is a great plug in. Whenever I needed help, or wanted to try figure out something it was all in Japanese. My impression was time tracking was a private person plug in, has this changed (Question 1)?

This is my version of red mine I am currently running:

Environment:
Redmine version 2.4.2.stable
Ruby version 1.9.3-p484 (2013-11-22) [x86_64-linux]
Rails version 3.2.16
Environment production
Database adapter MySQL
Redmine plugins:
redmine_work_time 0.3.1

Question 2:
I would really love to be able to start and stop like a stop watch to track time, like this feature:
http://www.redmine.org/attachments/download/773/timelogging.PNG
(from this entry http://www.redmine.org/issues/1650)
But don't understand how to get it. Has it or something similar been built into redmine?

Question 3:
My friend likes to do lists her can tick, is this the recommended way to go:
https://www.redmine.org/plugins/redmine_issue_todo_lists

I am thinking I must just take the plunge and spend a weekend trying to upgrade my redmine and modernize it a bit.

Thanks for any insight.