Don't think that one particular out of state market will shoot you to success or abject failure.

If a Chicago landlord’s failure to deliver possession to the tenant is willful, the tenant may recover up to the greater of two months’ rent or twice the damages sustained by the tenant.Can I get in deep waters here even with clause 7 above?

It protects them from failure.  

I don't regret the failures at all. 

But I primarily do failure to pay rent cases in Prince George's County and I'm in Anne Arundel County much less often.  

You really need to have a system for dealing with security deposits or you can face various liabilities (e.g. being liable for twice the amount of security deposit, failure of being able to hold the tenant responsible for damages using the security deposit, etc.).

I would also note a Quit for failure to provide inspection/showing of unit with proper notice. 

I can always use subsequent rental income to replenish the cap-ex "fund" and it's unlikely that I'm going to have a roof failure AND 3 HVAC units completely die out AND have to resurface the shared parking all in the same month. 

I’d like to hear about your successes and failures.2.

@Faraad Mohamed welcome to the market and I dig your post.You seem to be doing things the right way, and learning from your failures.