In turn, you would raise the annual NOI.

That seems weird to me and would raise red flags for auditors and I want to persue this in the best knowledgeable way possible.  

You are seeing it already, the nicely renovated units are having to compete on price with vintage units, because we are in a market where a lot of people are worried about their job prospects, not anticipating getting raises, on top of groceries costing 30% more than they used to.  

The are I grew up in declined severely and I am hoping to do what I can to give back to the community and raise the property values.

I had let my guard down and given a tenant the benefit of the doubt (a tenant who is (now was) a CEO and raised millions of dollars for a newsworthy venture).

I would raise both the same amount.

@Nathan GesnerYes the long term tenant is under market and I plan on gradually raising his rent.The other tenant is going through a divorce and is looking to buy a home.

It would mean the costs are financed with the property and it raises your basis cost against future cap gains.  

Ultimately I just raised rents and got better with outsourcing the maintenance in a cost effective way (wasn't doing that very well before).

Vote for politicians who won't raise the money supply by 40% again.