Roosevelt Documents - handwriting help needed

I have a few tricky bits stumping me in the two documents below.  If Henry Rosenberg or anyone else can help finalize them that would be great -- Thanks for any help!

https://crowd.loc.gov/campaigns/rough-rider-bull-moose-theodore-roosevelt/twilight/mss382990082/mss382990082-801/

https://crowd.loc.gov/campaigns/rough-rider-bull-moose-theodore-roosevelt/twilight/mss382990082/mss382990082-784/