Need Help Identifying A Couple Stamps

Just inherited a stamp collection and a Scott price guide, however I'm still having trouble identifying which variant I'm looking at with a lot of these stamps. So I figured I'd ask the experts here in this forum. Any advice would be appreciated, thanks.

In this first stamp, I'm pretty sure it's a Scott 68, but I'm not exactly sure which variant:



In this second stamp I'm really having trouble making out the writing at the top of the sleeve. I was hoping someone in the know could decipher it:

Top description on the second stamp has correct Scott number but the rest is bogus. Stamp is used not OG NH original gum never hinged. It is used and cat. $25 but the condition/centering lowers the value.

The writing above the second one appears to be describing a different stamp. While the "288" is accurate, that is a Scott #288, the words "Jumbo OG NH" and the "$300" lead me to think there was a different #288 housed in this sleeve at one time. It would've been an unused version of the stamp you have.

Thanks so much for your advice, really appreciate it.

The top stamp appears damaged -- it has a cut top edge, rather than a straight edge as some were issued with. The edge slopes down from left to right.