Party is on Saturday afternoon.

I have already started baking my cake and freezing them.
I work full time 8 hrs a day and have little time at night to work on cakes after dinner is made and kids school homework is finished.

I'm rolling fondant over my cakes.. I am hand painting one of my cakes and needs it dried by Friday afternoon.

I only have tonight, tomorrow night and Friday early morning to put the cake together. Than Friday when the kids get off school we plan to leave for the party.

My Plans Are:
Tonight I will finish baking my cakes, and start putting the fillings in the cakes and put it in the fridge. Also rolled the 9x13 cake in fondant and hand paint it to dried. (It won't be a problem to let it sit and dried for party on Saturday right? that would mean 3 days of cake sitting out) I'm afraid if I waited to paint on this cake I would waste too much time. Also I have to pack and get ready for the trip.. I don't have that much time

Tomorrow night (Thursday) I'm rolling fondant over my half sheet cake and decorating what I can. And will do my finish touch when I get to there (Friday Night).

Is it too early to put fondant on the cake and paint the one cake if I started tonight? The reason why is because Friday afternoon I am traveling 4 hrs to the party and won't get there till 8 in the evening.

So I am baking one half sheet cake covered in fondant and one 9x13 cake covered in fondant. the 9x13 cake will be painted and need time to dried.

If I understand your timeline correctly, it should be fine.

Fondant can be at room temp. for weeks and that is not a problem. The main concern is the cake inside or under it, which I do not know what it is. As long as there is no mousse or whiped cream inside your cake as filling, then that should be fine.