Now another issue has arisen. The previous two times I wrote to my potential boss, I had housing in NYC, (the city of the internship) more or less figured out. I had plans to rent a studio with a friend. To make a long story short, she basically flaked out, screwing me over. I couldn't afford the studio alone, and at the time, I didn't know anyone else who I could potentially rent it with. So I forgot about living in that studio.
Fast forward to now: I'm frantically looking for housing when a friend who I hadn't talked to in awhile calls saying that he is also looking for housing, and plans on finding and securing a place by the end of this week. Perfect timing. We agree to live together.
Problem: Around this time, most if not all move-in dates for apartments would be September 1st, which overlaps with the start date I indicated to my future boss. Ideally, I would (and I'm sure most people would also) want to get settled into my new living space at least 2-3 days before I have to begin such commitments as work (especially after moving to a brand new city).
Question: Do you think that, in this case, it would be appropriate for me to write to my future boss, briefly explain my housing situation, and ask if I can start my internship the day after Labor Day? Or would the fact that I'm requesting more or less a third date change indicate to her that I'm flakey and unreliable?