집에 언제 들여보내줄래? 집에 언제 들어가게 해줄래? 집에 언제 안으로 가게 해줄래? 집에 언제 들어갈 수 있게 해줄래? Depending on who is speaking, I guess which words they use would be different. They are all the same meaning so you don't really need to think which one is better or natural:)

네, It makes sense.