He basically said it was way more hassle than it was worth because of the extra filings because it makes me an scorp now.

If he' still looking (and $2mil in value is a lot to replace via a 1031, esp if he's looking into multiple props), then you may be able to negotiate with him so that you have a contract but don't close until a little further out, giving him a bit of extra time to get his ducks in a row. 

She told me she thought the cleaning fee was just a way for the host to pocket extra money and I was supposed to clean the property before I left!

My father and I think that IF we can not add an extra room in the home with what is already there, that we could possibly add about 250 extra sqft to the property.

@Sherwin Vargas thanks for the extra information.

Is it worth the couple extra hundred bucks?

I want a C-corp to keep my schedule E cleaned up to be attractive to lenders, I want that extra w-2 income form the C-corp.  

I agree with the previous poster that this probably isn't going to be a long term rental anyways, so this extra will just add a cushion to your turnover costs.

Also worth pulling past permits.How much value an extra bath brings really depends on the area.

Capital Gains taxes can be avoided using 1031 exchanges, so the extra risk doesn't seem to make sense.That being said, if I found a deal and it happened to be in an OZ, cool.