Earnings that pay for repainting, flooring, new hot water heaters, and perhaps will qualify you to get another property..

Assume cost to repaint and clean between tenant turnover is $1500 per unit.

I had just repainted his apartment before he moved in.

The trick is learning that number.I pay:Interior repaint (3 colors): $1.5 - $2Flooring: $1.5 Roofing: $300 (all in materials and labor no deck repair)Windows: $75 per openingHvac: Condenser/a coil = $3k furnace = 3k (high, but I get priority and zero upcharge ever)All new pex $1500That's a basic list, but you get the idea.

Complete repaint on the inside.

He was deducting money to repaint his kitchen without notifying me when previous paint was done 5 years ago. 

Let's say you have to repaint every two years, get the carpets cleaned (and/or hardwoods refinished) every two years, replace the carpet every 5 years, fix broken cabinets/appliances/plumbing fixtures/light fixtures, etc.

Granted, we are currently in the month of February, and the weather is not currently suitable to adequately scrape, prime, and repaint the areas of concern on the front porch.

we set our cap ex budget by getting quotes on roof replacement, exterior painting, etc factored in the life span + increases for inflation (e.g, we assume its going to cost more to repaint in 10 years then it is today, so we factor that inflation into our calc) to derive an annual accrual amount on cap ex.  

Can someone post their opinion if the Landlord (homeowner) can actually withhold some of the deposit.The Landlord will return the Security Deposit at the end of this tenancy, less such deductions as provided in this Lease but no deduction will be made for damage due to reasonable wear and tear nor for any deduction prohibited by the Act.During the Term of this Lease or after its termination, the Landlord may charge the Tenant or make deductions from the Security Deposit for any or all of the following:Repair of walls due to large nails or any unreasonable number of holes in the walls including the repainting of such damaged walls;Repairing cuts, burns, or water damage to tile, linoleum, carpet and other areas;Repainting required to repair the results of any other improper use or excessive damage by the Tenant;Repairs and replacement required where windows are left open which have caused plumbing to freeze, or rain or water damage to floors or walls; andReplacing damaged or missing doors, windows, screens, mirrors or light fixtures;Any other repairs or cleaning due to any damage beyond normal wear and tear caused or permitted by the Tenant or by any person whom the Tenant is responsible for;Unplugging toilets, sinks and drains;Any other purpose allowed under this Lease or the Act.