For your first scenario, I think it mainly depends on the reason as to why someone feels/acts the way they do.
Posh: "Mr. Mason is just as posh as ever. He claims he needs the most expensive utensils to eat and refuses to go barefoot on any floor that is not of good quality wood."
Squeamish: "Kelly couldn't stand walking barefoot on any surface that is dirty. Just the thought of dirt, dust, and anything gross between her toes made her feel nauseous!"
Fussy: "Bonnie's son was extremely fussy about his food. He wouldn't eat anything that wasn't salty or that was any color he didn't like. What a picky child!"
There are many different words you can use depending on information given about the person.
For your second question, the first one makes a bit more sense (Today makes it three).
Person #1: "You're kicking me out because I am two months behind on rent?"
Person #2: "Well, today makes that three months, so thanks for reminding me!"
Sounds good to me!