Hello again! Sorry for the delay in response.
If you only plan to use a web browser and visit various web pages, Tor and a VPN program such as Hotspot Shield will work almost the same. The main difference between Tor and a VPN program such as Hotspot Shield is that Tor only protects web browsing and VPN protects all programs on the computer. To explain this better, let's say you use a web browser for surfing and a file download program to download files from the Internet, for example Torrent.
With Tor, you get a special pre-configured web browser you need to use in order for your computer to be anonymous when surfing the Internet. That means the usual web browser, such as Safari, won't work. Also, when you start Torrent to download files, it won't go through Tor, so you won't be anonymous.
With a VPN program, such as Hotspot Shield, you can use any web browser for surfing the Internet since it doesn't just modify the settings in a web browser, but it modifies your computer network settings. It means all the communication coming from your computer, no matter if you use a web browser or a file download program, will go through a secure VPN server which provides both security and anonymity.
So, as you can see, VPN is far more advanced than Tor; however, it all depends on what you plan to do.
Note that Tor is free to use and VPN is usually not. Hotspot Shield is among a few VPN programs that are free to use, but you may occasionally see ads. Also, a free version will only connect to a USA VPN server. If you want to connect to other country's VPN servers (and therefore get their IP address instead of the USA one), you will need to upgrade to Hotspot Shield Elite.
See the prices for the Elite version here:
Regarding the e-mail address:
If I were you, I wouldn't use my private e-mail address with strangers or when registering to some new chat web sites. Go ahead and create a new e-mail address that you will be using only for that purpose, for example a new GMail address. For added security, only access that new e-mail address when using Tor or VPN, and access your private e-mail address using a standard connection.
I hope this helps! You can try with both Tor and VPN (Hotspot Shield) and see which one is easier and better for you.
For further questions, I am here to assist you.