Office 98 works well on both 5300s and 1400s. Also WordPerfect 3.1.

I think you might be able to use 8.0 and 8.1 with that level of RAM. 8.6, no, I think you would want to have 40+ MB hard RAM running.

I have two 5300s, both cs models, that still run fine...I like the keyboards on the 1400 series better, but the 5300 is a nice form factor. Better hinge design than the 1400, that's for sure.