When someone wants to attach a file then the window repaints with the needed fields.

She also said that it will seal in any pet odors we aren't able to remove from washing.However, others have said it's not worth the expense, and if tenants decide to paint the wall (without permission), we will have to incur the cost to re-paint with the same expensive oil-based paint. 

I'm partial to an eggshell white for a clean look, but I know it's not about what "I" think, it's the average customer/tenant (do you re-paint to match trends or go neutral?).

Repainted doors.

Tenant(s) and or guests that violate this do so with the understanding that smoke damage can costs thousands of dollars (including replacement of flooring, light fixtures, window coverings and repainting of the premises) to remedy and Tenant(s) shall be responsible for associated costs.To answer your question, I think you should try to charge the tenant for everything you listed--whether she will ever pay it is another matter.

I got hit with partial repaints because tenant had posters that got pulled down and cracked paint (no chipping paint allowed).

I agree with Travis, If you dont have to spend $10k renovating in order to increase $300 a month that will take you 3years to get those 10k back IF you maintain a 3 year lease with no interruptions (no new tenants where you have to spend money repainting walls and shampooing carpets) I would say keep the 14year long tenant. of course if the numbers work. 

Needs a repaint bad. 

A burly gent with a saws all would make quick work of it if it were mine.I know these old timers make comfy bathtubs for those who like to soak--nice and deep-but the sides are tall, requiring a large step over and to me the antique look is not something I want to offer the market.A shower with a surround can be a relativity easy install and makes the unit from what I would consider a "Boutique" or (lower income) offering to a more mainstream modern offering.Personally I would not rent a unit with a claw tub for myself to live in.A shower with a spray wand attachment and a mixing valve setup is a modern offering.And for a unit that might appeal more to those with tikes in the house, a bathtub with a surround would be my choice.But of course if money is the issue another repainting might solve the problem, especially if you cannot raise the rent with a more modern offering.Are the current renters tub soakers who love this setup?

The best you can get is a family that doesn't have a history of evictions, criminal convictions, or slip and fall lawsuits against landlords (you'd be surprised how very common these are), who is able to use their earned income tax credit for the deposit.If you had a property that was in poor cosmetic condition already, that needed to be repainted, needed new flooring, needed new kitchens and bathrooms, already had a ruined lawn/driveway, and you planned to run it into the ground renting to Sec 8 for many years, then either renovate to sell, or sell it in "as is" condition, sure.