Single cut path for cursive?

Hi, I'm still fairly new to Adobe and I have an ancient version, which doesn't help anything.

Anyway, I'm trying to make a two layer vinyl decals for a friend's business. They want this cursive font, but I'm running into a couple problems...

#1. This cursive font seems to suck! It seems like it's just letters crammed up to one another to make it "cursive". Whenever I select the font, you can see where the cut paths are running into the next letter. How do I change this!? I need just one solid cut path, not all these little lines everywhere!

#2. When I offset the path to make the background text proportionally bigger, same thing

..the cut paths are on other letters. I pretty much just need it to be one big bubble behind the top text.

#3. I noticed that the top text doesn't look like cursive. Well that's because the "intersect" isnt showing up?

Pleaaaaaseeee! Someone who knows what they're doing! Help me! These friends have been asking for these stickers for a while and I've been putting them off because they're challenging me and now it's time I bite the bullet and figure it out!

Thanks!