We've been living in our apartment for about a year and a half. It's a decent apartment in terms of the layout and bare bones, but it's been trashed and poorly taken care of by previous tenants. We've gotten our cabinets and kitchen sink replaced, and we have a list of repairs for the landlord once we officially resign the lease this week (namely, need some regrouting in the bathroom and kitchen, a screen in the bathroom needs to be replaced, the bathroom sink is leaky, etc; little things, nothing we broke). Our landlord is a pretty good landlord by Boston standards, which means that he responds to complaints very quickly, fixes stuff when asked, and doesn't engage in any obviously super illegal practices.
The problem?
Previous tenants painted the apartment horrible colors, and put tons and tons of holes in the walls. No one's been taking care of the place, so the trim and the doors need to be repainted as well; they're full of cracks and practically unwashable (we've tried). Some of the holes in the walls were made with drywall anchors that have been painted over, making them difficult to remove.
We were told by the realtor that the apartment would be repainted, but 1) we're not surprised he lied, and 2) the biggest eyesore (the checkered flags painted on the living room wall) were indeed painted over by the previous tenants before they moved out. The landlord did tell us that he would pay for supplies if we wanted to spackle and repaint, but the problem is that the task is overwhelming.
A year and a half later, with 1-2 more years in this apartment on the horizon, I tired of it being really gross. I'd like to hang stuff on the walls, but it's hard to do so when there are holes, old nails, and painted-over drywall anchors all over the walls. It's hard to feel like we live in a home when the walls have grime on them that we can't wash off. I would be fine repainting just a room or two, but this isn't a matter of repainting 4 walls.
Thinking, "I'll charge him for supplies, and spend 2-3 weeks repainting this summer," I asked for advice on social media, along the lines of, "How do I do this REALLY quickly and efficiently?" The overwhelming response has been, "UM, haha no, you really should be trying to get the landlord to redo it."
So ... I guess I'm just not sure HOW. I'll check the details of the lease when I get home, but I know we didn't get in writing that the apartment would be repainted. I'd honestly prefer that the landlord do it himself, since it'll happen better and faster, but my friends also suggested that we ask for a massive deduction on rent. (Which then leads to the question: How much would it cost to have a 690 sq ft apartment entirely repainted?)
ANY advice appreciated. I'm totally used to living in crappy Boston apartments, but J is adamant that we not move, and I'm just done with living in crappy apartments.
now with ~* INCREASED SASSINESS *~

Re: NWR: Convincing (Boston) landlord to repaint apartment
Could the landlord be unaware of the problem?
First I would simply ask that the landlord cover the cost of the repair and repainting of the whole apartment (including door and trim if those are part of the paint issues).
If he says no offer to do the work yourself if you can deduct the supplies and $x per hour of your time (each of you) to do it yourself from the rent. You would need to track your hours and keep receipts but doing it yourself would ensure it gets done.
If he still doesn't then you will have to suck it up and eat the cost and time if you really want it done (assuming that there is nothing in your contract to force him to do it).
Painting and patching is tedius, but not hard. If the walls are grimy you will want to prime first, or at least buy a paint that has primer in it. For the wall that is painted in a checkerboard pattern you will want to lightly sand all of the lines and prime before you paint. Otherwise the pattern still might bleed through.
@phira If the damage and amount of work that is needed is as extensive as you say I think it would be worth his while to have it done right, especially if you can prove you are good tenants who pay rent on time, take care of the apartment and don't cause trouble.
Would you be willing to sign a longer lease if he agrees? That might be worth it to him to keep good tenants for two years (or whatever) than risk losing you over something so simple.