Added what translation I could. 箱【はこ】is the character used for 98/98SE, meaning "box" but I have no idea how that relates. Can also mean "sheltered" depending on context.
"Abomination" for 禍 is probably a bit colorful, but I think it captures the idea.
Not sure what to do with the text in the corner, 非公認 = unofficial, unauthorized, unlicenced or unaccredited. As for Meでもわかる = Me But you understand (or know). Anyhow, if anyone feels like it add a translation for the text in the corner. I can't make out a good translation from what I know...
OldFrozenReliableWoof woofNT Workstation
いぬてぃ -> inu-t -> NT
Used for some version of Windows NT Workstation for some reason...Fish
魚 -> さかな -> sakana -> fishBox
箱 -> はこ -> hako -> boxFairyAbominationMackerel
鯖 -> さば -> sabu -> mackerel
The pun is that 'saba' and 'server' sound similarPregnant
妊 -> にん -> nin -> pregnant
妊 is most likely short form of:
妊婦 -> にんぷ -> ninpu -> pregnant woman
Breathing with gills
鰓 -> えら -> era -> gills
呼吸 -> こきゅう -> kokyuu -> breathOS memory comparisonEat
(referring to XP's tendency to eat up memory)Dog
犬 -> いぬ -> inu -> dogRun away!"" Unofficial That Even ME Can UnderstandNijiura