Your thought on the security deposit

[Matt Rasich]

Hi guys. My name is Matt and currently my wife and I have been living at the same apartment in Chicago for 3 years -- never late on rent. 

Long story short: My landlord raised the rent by $40 year two and $60 year three but two months ago (a week before our wedding) he let us know he'll be raising rent by $250. He came into our apt, with notice, two days before our wedding to take pictures. I was at my bachelor party while my wife was crafting center pieces and our landlord made her cry because of how the apt looked stating "this is a business!" There was no damage to our place, but it was full of wedding gifts and supplies. I've been searching the web for information, which thankfully led me to find BiggerPockets.

Needless to say we are moving out to another apt in a few days and I'd like to get your thoughts (tenants & landlords) who have gone through the issue of security deposit multiple times.

I would like to know the thought process of a landlord and what you would look for while walking through the apartment.

Do many landlords use a walkthrough checklist and what would it look like?

Any tenants out there who have had good and/or bad experiences with retaining your security deposits? Any success stories?

I feel I would need something in writing to cover our backs. I'd love your input since this is the first time dealing with this type of situation.