I suggest you get in the habit of eating vegan before you make the commitment. Stuff like, start cooking vegan meals now, finding recipes you like, trying out different vegan substitutes, locating convenience-type vegan options available to you, etc. That will make it a lot easier on you when you commit to veganism, because you won’t find yourself hungry and out of ideas and desperate. Also think about how just vegan you want to be – make those big decisions beforehand, like will you eat honey? gelatin? wear wool? etc. I think the more you take your time and plan ahead, the easier it will be for you, the less stressful.
As for loving dairy, I don’t know if anything can replace cheese, but I’m a BIG fan of ice cream, but I’ve found two great vegan substitutes: coconut ice cream (seriously amazing – I’m not vegan, but I love this stuff, sometimes I choose it over real ice cream), and for ice cream sandwich bars, there are a few brands of soy ice cream versions out there (like “Cuties”) that are really good (although I wouldn’t eat a bowl of soy ice cream)