.- this kind of question would raise eyebrow if being asked in Asia.- In asia country the only question is "Shall I take Master or Phd".

Tenant didn't have a pool, so the huge spike raised an eyebrow.

I think a lot of people have since built in there and you can't really camp on land there without getting raised eyebrows from neighbors.Depending on location, this could be a really good play. 

Lenders will take leases for a room provided you have a lease in place.The addressing is the only thing I see in your post that may raise eyebrows, but even then, I've seen it go through both ways... really may come down to the lender.Cheers!

Then it will probably stay an “airbnb” I also don’t think 3 to 4 homes in any market in any asset class is enough to raise an eyebrow. 

The fact you mention square footage raises an eyebrow. 

They would also be able to point out certain red flags like structural concerns that raise some eyebrows.

Bucktown- I know a lot of seasoned investors will raise their eyebrow with me mentioning Bucktown due to the fact that it is pretty much already booming and the prices are on the higher side, but I will say if you can find a good deal in Bucktown, please jump on it.

It just doesn't add up well and they will raise a few eyebrows.

I imagine a single transfer of the full amount will raise eyebrows.