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A lot of the "old games" issues can be addressed via remakes or emulators with throttling. For example, here's a very nice remake of Head over Heels for PC, Mac and Linux.

Then about getting stuck, there is the Net... a lot of FAQs for old games are lying around. It's a bit cheating, true, but if you are really stuck to the point of the game not being fun anymore, it can get you out of there.
Same can be said about number of lives... there are many cheating devices / software that allow you to make things easier. As long as you have fun (which is the point of a game), it doesn't matter if you cheat or not (if in solo play - multiplayer is another story).

http://oolite.aegidian.org/
http://retrospec.sgn.net/users/tomcat/miodrag/xEli te.zip?
http://www.rebelstar.cd2.com/cgi-bin/dc.cgi?file=r emakes/elite_-_the_new_kind_v1_0.zip

May I also recommend:

Privateer...
http://priv.solsector.net/
http://wcuniverse.sourceforge.net/

There's already a remake of Skool Daze, called "Klass of 99", but it's a straight remake, which i suspect is not the kind you had in mind?

Has been remade before as Klass of 99 - which is very close to the original.

Funnily enough, the only thing educational I remember about the original was it was set in an educational institution. It was inspired by those early to mid twentieth century British schoolboy tales of japes and pranks.

Nah, you're not the only one.
Just damn near it.
(There's a nice remake for windows, BTW)

For a start, here's a list of the games he made on the C64.

Before he got a C64 he was writing for the Speccy (with games such as Headbanger's Heaven) and Atari. Since then, he has worked with the Amiga, the ST, the Jaguar, PCs...

Retro outfit Retrospec have made a number of tributes to his games.

HAL

You can play a remake of HoH make by Retrospec (freeware; Windows, Linux and Mac versions available)

There's even a Luni.. err Linux port; sadly it is x86 only.

Actually, Allegro's official homepage is http://alleg.sourceforge.net/ Allegro started off on DOS, but there are now fully fledged ports to Unix (Linux, FreeBSD, Irix, Solaris, Darwin), Windows, QNX, BeOS and MacOS X. One of the differences between Allegro and SDL is that Allegro is a higher level library than SDL, meaning that it takes less code to accomplish certain tasks at the expense of some (but not much) control. Also, there's more to Allegro than SDL (such as data-file managment and a GUI, although the Allegro GUI looks awful, but you can substitute your own GUI). In fact, there's even been talk of porting Allegro over to SDL so that it runs on top of SDL. Allegro is truly excellent for 2D games. It's built in 3D is somewhat lacking, but there's a tweaked version of OpenGL called AllegroGL available that lets you use some OpenGL functionality within Allegro. An example of a game written with Allegro is this re-make of "Head over Heels". It's an Isometric 3D game featuring shadow casting, real-time lighting and transparency. Sound, graphics and coding are done by professionals in the gaming industry. Allegro is a Sourceforge project and the development is very active. Some of the core developpers have jobs in the industry and work on Allegro in their spare time. In fact, an Allegro community has sprung up and can be found on the following website: http://www.allegro.cc. As well as many lively discussions, there's also a vast collection of projects written using Allegro and other members of the community get to rate the projects.

On an almost on-topic note, I've gotta point out this site.

The spectrum had some of the coolest games ever, and the guys at Retrospec have made some great remakes. For those of you who were unfortunate enough to never have a Spectrum, I'd especially recommend any of the versions of Manic Miner, and Klass of '99 (a remake of Skool Daze).

I'm sure I still have a working Spectrum around here somewhere...