Is it that big a deal on that small a screen?

Yes, the highest possible for the PSP with Sony Image Converter 2 is pretty fast. I convert movies for my Palm at an even higher 480X320 resolution with Kinoma Producer and it still doesn't take more than 30-40 minutes.

UMD is better, but not enough to shell out an extra $15 for when I will probably only watch the movie portable once or twice.

I'd be surprised if it was only 30 minutes total to rip a DVD to the memory card, as it almost takes me that long for DVDShrink to rip a DVD image (sans the extras and multiple soundtracks) to my computer, then usually takes another 30+ minutes to do the encode, and then there is the time to write the new image. Granted my computer is not new (8x DVD, 1.6Ghz processor), but I'm not going to buy a new computer just to rip DVDs faster.

darkside, I'd be curious for you or someone to time the whole process from the point of having the DVD in your hand to watching the first seconds of the movie on your PSP. Plus I'd like to know what the size of the final image is at the highest resolution, 30fps, reasonably high level of sound. Try Million Dollar Baby tomorrow perhaps as an example movie.

Updated list of movies available/announced:
4/19 XXX, Resident Evil Apocalypse, Hellboy, Once Upon a Time in Mexico, House of Flying Daggers, Kill Bill Vol 1, Pirates of the Caribbean, Spider-Man 2
5/3 Reign of Fire, Hero, National Treasure
5/24 Are We There Yet?, Charlies Angels
5/31 Hollow Man, Boogeyman
6/7 Terminator 2, Van Wilder, Punisher, Saw, Open Water
6/14 Spider-Man: Animated Series, Daddy Day Care, Hitch, Bad Boys, Grudge
6/21 King Arthur DC, Hostage, Cursed UR, Tron
6/28 Air Force One, Crouching Tiger Hidden Dragon, Resident Evil, Starship Troopers, 7 Seconds, Short Circuit, Dreamscape, Endless Summer, Super Speedway
7/5 Napoleon Dynamite, I Robot, Predator, Super Troopers, Dodgeball, Appleseed
7/12 Black Hawk Down, Anacondas, You Got Served
7/19 Kill Bill 2, Armageddon, Gone in 60 Seconds DC, From Dusk Til Dawn, Man of the House, Oldboy
7/26 XXX State of the Union, Dark Crystal, Labyrinth, Not Another Teen Movie UR, Final Fantasy Spirits Within, Monty Python & Holy Grail, Cowboy Bebop The Movie, Assault on Precinct 13 (2005), Assault on Precinct 13 (1976), Chronicles of Riddick UR, Dawn of the Dead UR, Fast and the Furious, Rundown, Van Helsing, Steamboy DC
8/2 Big Daddy, Guess Who, Ghostbusters, SWAT
8/9 Kung Fu Hustle, Team America World Police, Coach Carter, Without a Paddle, Replacement Killers
8/16 League of Extraordinary Gentlemen, Coyote Ugly DC, Sin City, The Rock, Shaolin Soccer, Big Hit, Richard Pryor Live on Sunset Strip
8/23 Layer Cake, Snatch, Time Bandits, Total Recall, Young Guns, Cabin Fever, House of 1000 Corpses, House of the Dead, Evil Dead, Halloween, Ninja Scroll, Ghost in the Shell, Blood: The Last Vampire
8/30 Sahara, Friday Night Lights, Bourne Identity, Italian Job, Transporter, American Pie UR
9/13 13 Going on 30, Akira, Beauty Shop, Be Cool, Bulletproof Monk
9/20 The Longest Yard, American Pie 2 UR, Mr Deeds, Pitch Black UR, Gone in 60 Seconds (1974)
9/27 Robots, Amityville Horror (2005), Barbershop, Bill & Ted's Excellent Adventure
10/4 Tomb Raider, Tomb Raider Cradle of Life, Star Trek Nemesis, Warriors DC, Knight's Tale, Never Die Alone, Ong Bak Thai Warrior
10/11 Unleashed, American Wedding, Kingdom of Heaven