Legality is a question best asked to your lawyer, the laws are currently fluid in most of the world and they change frequently - free legal advice on the Internet is often waaaaay too expensive. However, if you don’t share the resultant files, don’t resell the DVD, and don’t broadcast the video typically you can argue what’s called “fair use” - essentially it makes no difference if you’re too lazy to pick up the DVD and put it into your player, you own the rights to the movie and you’re still using it for personal use. How successful this argument is depends on your lawyer and country of origin
As for the player, I use a mixture of DVD-WMV and DVD-Fab Platinum Mobile to convert to WMV files that can play on Windows Media Player or be streamed to my XBox 360. Both are great tools and have distinct “personalities”.