Originally posted by @Andrew B.

I'd answer those questions first, and then have that lead to your answer. 

Since I think we can all agree on the answer as no - a court would not look at that as an arms length transaction and thus give you zero asset protection (note not a lawyer just someone with some common sense)

Once it was repaired the new work didn’t really do anything to increase the value of the property, just repaired the damage to its original state.

Well, to answer that question you need to look at the influx of people in the different tourisitc hotspots in the city over the last x months/years.

@Madan Gowda have youbfind some answer to your question.

Once I graduate, I'll hopefully find a buyer who is offering more for the property than I originally planned to buy it for, that way, I can use the difference to pay off my tuition.Will this be feasible in the Boston University area?

They will make you replace windows with the exact same product as the original windows, same with exterior trim and roof.

That leads to your answer: What are you doing to find owners who are willing to sell under market?

I can answer these questions but it’s bit involved for a post.