Many factors to consider like - Can the residents afford an increase, are they great residents, am I getting a decent ROI, do I want to create the risk of turnover, etc. 

But the name of the game is skate to where the puck is going....this market seems to have a vibe of affordable housing, space, yard, single family, etc... in my opinion Not sure about NY, but Cleveland has pockets of massive appreciation.Tremont, Lakewood, Ohio city - all neighborhoods of 2x-4x appreciation over 7-10 year horizon..... not sure now as I never had the stomach for the risk/reward.I always operate in the same market since I’m a high velocity flipper and deals exist all over the Midwest key is building relationships and trust in your market.

Get them both to at least acknowledge it, and her to sign a new lease with just her on it, you probably also want to verify that she can afford the unit without her husband's contribution, she obviously thinks she can but you also don't want her paying 75% of her income towards rent.

But if you take the profit margins out from others to do so does that not prevent them from being able to afford to do those same efficient upgrades?

(The fact that symphony musicians cannot afford the lifestyle where tuxedoes are worn was not considered.)

@Anthony WalkerIf you can afford it, let a property management (PM) do it for you.

I can certainly spend a lot of time researching and DIY, or use an affordable online service, or I can sign up with knowledgeable advisors that cost thousands.My question is how much net worth do you think one should have to justify getting the pricey advisor's service? 

They will be able to advise on the plan requirements, potentially giving you something off the shelf from a previous project or referring you to an affordable draftsman.

@An Duong it's really up to you whether it's a good enough deal for you to agree to that.I will say, besides the two years of below-market rent, you should also factor the cost of an eviction into your thinking.It may not end with an eviction, and if it doesn't then you'll have saved some money, but I would go into it with the assumption you'll have to do one since I think there's a non-negligible chance of that.In a negotiation, sometimes it can be helpful to try to figure out the other person's motivations and find other ways to meet it.For example, if he's worried about being able to afford market rent, then if it's $200 below market a month, and you don't want to tie the unit up for a second year, maybe you offer to pay $2400 more at closing and only have him there for one year.If he really likes the area, maybe you find him an apartment in the area and offer to pay his security deposit, a moving company, and X months of rent to get him started.

I am very curious about how a FHA loan works because we could not afford a large downpayment if anyone has more details on that, that would be awesome!