I misread the diagram this morning. I thought you were going to penatrate the wall ABOVE grade. If you DO penetrate above grade you will avoid the potential water leak and you will have a source for future outdoor electrical
Instead, use a 4square box. You have more room for the splice, you can ground it and you can add to it. Transition to 1/2" emt up the wall. (anything over 18" of PVC looks bad). No real need for the second box up top...just sleeve the romex down the wall.....OR....extend the 3/4 conduit up the wall and put a 4s box up high.
There is always several ways to run pipe/wire. I don't usualy decide till I get there and have a real look at things.
PS. I said NEVER use UF because A) it's is vulnerable underground, B) you can't replace it if it faults or add to it, C) it is difficult to work with (strip sheathing)