Repair of an appliance, painting a room, replacing a door lock are a few examples.  

In 8 years, I've replaced the D battery 2 times (every 3 years) and it lets you know weeks in advance (red light after entry) when it's going to die.

My hope is to keep that process going (HELOC for flips, profits for buy and holds) until I have enough rentals cash flowing to replace my current income.

Is becoming a real estate agent a realistic option to replace my current w2?

Hi Serj,When it comes to insuring your property, it is always best to insure it for the full replacement cost.

My goals are to replace my income from the restaurant with passive streams of income from investment properties.  

Most original wood windows need to be replaced, HVAC will need to be installed, both kitchens need updated, all bathrooms can use updates, painting all around, refinishing the original hardwood floors, adding new/nicer carpet in the bedrooms. 

Fully replacing things is where it can get hairy, as sometimes you can expense some items in full, and sometimes you're better off depreciating those items over time (but not necessarily included with the depreciation of the building itself).

Be certain to account for any security or last months rent deposits.The tenants may be willing to sign a new lease to replace the old one if there is something in it for them.

I would also add removing old,broken,warn out,or enormous furniture that is clearly unattractive and makes the living room and bedrooms appear smaller and less comfortable than they really are.The house should be staged with modern and appropriate furniture to show buyers what they're new furniture will look like in their new home.Excess clothing that is not normally worn should removed from overstuffed closets and dressers and donated to charity,thrown away,or boxed up and stored off site from the home.If your toilets are old or have unremovable stains that look terrible,replace the entire toilet.Bathtubs should be reglazed to look shiny and new again.