Water, Trash, common electrical? 

We spent a month cleaning the place up (this including getting the pool cleaned, replacing everything in both bathrooms, redoing the kitchen, painting and generally just making it liveable. 

Yes keeping your units clean and updated( particularly kitchens and baths) will help you collect the higher side of your market rates...but realistically these updates should be ongoing and not a prime rent increasing tool.

The annual inspections are good I think, as it gets the tenant cleaning up and keeping things proper in the unit.

I prefer class B properties which usually require clean deals. 

Electric baseboard heat and 1 wall AC unit per side.

No, mostly safety-exposed electrical, trip hazards, properly functioning electrical/plumbing, etc. and wood rot, peeling paint(sometimes) functioning kitchen appliances (only if they are present-not required), etc.

But the past couple of years whenever I go in to access repairs, I've noticed they are not clean people.

I would probably get the carpets cleaned if they look bad.

I recieved a judgement for 1400$ due march 31st and tenant leaves in 7 days or gets evicted with the verbal agreement she would sign a payment plan and leave the unit clean for giving her extra time as she had no where to go.