I will not be conducting any business in MA just collecting checks as I will have a property manager managing the property in NY.

Do I report the full amount I am "charging" and then somehow show that I collected less due to the discounts?

@JD Martin a long time voice of reason seems to say at least 75% empty.So either you ask for an extension or cancel the deal as I doubt a reasonable seller would take their property off the market that long. 

"As a third-party online payment facilitator, Innago is required to collect tax information for any taxable entity that receives more than $600 in payments.

You get the write off for the repairs and still collect 100% of the rent so there’s no question down the road about gat happened to the missing rent.

I want to start this thread to get ideas, opinions and valuable tips on how to do it RIGHT.Lately I have been reading on this subject ,extensively , and trying to learn as much as I could.

Third, I'd like to know what data I need to collect in order to write this off on taxes.

As consideration for the loan we are providing and to secure your obligations under this Agreement, you hereby grant to us a security interest in the following property (collectively “Collateral”):all consideration received from the collection, sale or other disposition of the Collateralized Goods, including any payment received from any insurer arising from any loss, damage or destruction of any Collateralized Goods and any other payment received as a result of possessing any Collateralized Goods, or any other proceeds of Collateralized Goods."

Would one - most senior tenant - be responsible to take care of the utilities, collecting payment from other tenants? 

We aren't using the garage at all and aren't planning on doing so, so we thought on making it a living space separated from the house for rent, which we'll sacrifice 1 of the bathrooms to add it to it, and later on do the same with 1 of the rooms as well, though I would have to make an extension to add the rest (kitchen, bathroom, etc.) so that way we could take advantage of the space we aren't using.