I tried setting up both exchange for work and my yahoo account on outlook 2010 and I kept getting a server connection error. I had no issues setting them up on outlook 2016 on my Windows 8.1 virtual machine so apparently older versions of outlook are blocked by some email providers and I actually found a yahoo help article stating that they have blocked older clients. I haven't tried my gmail or msn (outlook) accounts because I rarely touch those. Maybe tomorrow I can try with gmail and MSN but I suspect that they have also been blocked. If you wish to use an email client you might have to get a third party one like thunderbird.

Outside of that if you trust yourself with documents and are careful stay with what you know but if you want security go with 2013 or later. I would not go with 365 because of the subscription. If you don't want to pay for later versions but you want to get something that's updated go with free alternatives.