Usman Asar

you dont need to restart the webserver in case of Windows server, just recycle Application Pool (will take a blink of an eye) and you'll be good to go.

what I am wondering is, why is  it taking so long for plug-in to install, that it is  giving timeout error.

Just before you proceed with diagnosis, I would prefer referring you to an hour long video tutorial to learn how to properly setup Moodle on Windows Server

http://blog.academictools.org/2015/12/installing-moodle-on-microsoft-windows.html

Where you mentioned Server 2008 R2, have you not checked ISAPI and ISAPI filters? as since R2 Server 2008, PHP is handled by FastCGI so just selecting CGI in IIS options will suffice, ISAPI was used in older versions where PHP was handled by CGI that is  why PHP sites were running slow in Server 2003 era.

Lisa, though I personally haven't used MoodleCloud, but plenty of the community members do have accounts there for test purposes, and as I am aware, there isnt anything that you need to install additionally to make use of full moodle capabilities (in terms of course creation).

And I couldn't get it when you said you cant access localhost. is the site not opening?

Just for the sake of learning  more about Moodle, you may want to take the course  on Moodle starting from 7th August https://learn.moodle.net/course/view.php?id=10464

Adobe Animate is the new Flash

not everyone can do screen recording, but most of the people who cannot find any way to download directly (download link given), use browser based plug-ins or download accelerators that automatically senses the multimedia content (videos, audios) and let users download them with ease.

Though cant be made impossible, but very hard for those who uses third party plug-ins  and accelerators, by using streaming server capable of sending adaptive rate HLS or MPEG-DASH streams, that in turn rather than sending whole video down, send small chunks of 10 seconds, and they become nearly impossible to re-assemble at users end even if they download.

Just a thought if you want to give option of video protection to your clients.

I wish things would have been that automatic to do everything based on clicks, but they aren't.

after installation, you need to setup SMTP virtual box as well.

refer to this blogpost

http://blog.hyperfive.com/2013/07/how-to-setup-internal-smtp-service-for.html