If I want to get rid of all regulations, insurance, HOA fee, bylaw, etc, and write a 1-page HOA doc such as "There is no association.  

In my leases I clearly write and explain to tenants that we will remediate any issues uncovered in the 1st 30 days at our own expense.

@Christian Espana, If you have no cash flow then. you probably are not able to take advantage of depreciation write off as well. 

I would also make sure I gave him that in writing.

@Dean VelodotaThis arrangement sounds complicated.An LLC is an entity that is meant to hold business assets.A house-hack is normally an asset that is partially business and partially personal.I don't agree 100% that you can write off the expenses towards your side because that would mean you are attempting to deduct items that are personal in nature.Good luck with whatever decision you decide to report it for tax purposes.

I would verify (in writing) with your agent that the company allows rental to students.  

I thought for sure we would be able to write most of this off.

Write down the answer.

In my offers, if the property is rented, I require Addendum R to be completed and write in contingent upon tenant/landlord completing and buyer approving Estoppel as well as in some cases, providing previous year's tax returns and proof of payment for last 3-6 months for review/approval. 

As I write about in the below post, this is a bad idea in my layman's opinion.