Hi Sixstring,
I tried Anaconda one year ago on a 'old' pc, the sort you find at my school of interest :
- it was looking more slow than Winpython (probably because of the 2go Ram limitation of the PC)
- it was not 'python3' friendly, so would necessitate an internet connexion to finalize in python3,
(python 3 direct support has changed since 2014-05-29,
http://continuum.io/blog/anaconda-2-released, so point may be less relevant now)
- it is not a replacement of an usb installation, but you can create different virtual environnements,
- and you download a binary with only a md5 key to check.
Time has made these drawbacks weaker.