This elevated part is parallel to the sidewalk, meaning that you can't trip over it unless you decide to do a 90 degree turn to the street at this exact half of foot spot. 

I also read the city's master plan and they are working towards converting a popular street into a more pedestrian friendly walkway with sidewalk stores and restaurants.

Like sidewalks, a paver patio and gravel side yards with stepping stones.

You’re in a car accident, you didn’t know there was mold, you chose a gas appliance that exploded, you didn’t get the sidewalk cleared.

On the flip side trees can be a mess to clean up, fall and damage your property and can even invade sewer lines or lift sidewalks. 

Now winter comes and the tenant has not properly cleaned the sidewalks.

Some thoughts:1) The messed up front sidewalk is not helping your curb appeal.

Start with the end value of the buildings or lots and work backwards.Next check with the city or county to determine if you can do what you want to do and what is required for all zoning approvals and the time frame, Ask if you have to install curb, gutter, sidewalks, street signs, street lighting or any other special requirements. 

I recommend fixing the roots and the side walk.

I imagine the streets are torn up where your lot is in the North 1 project area so it might be worth waiting at least until they've installed the pipes in the street and built the new curb/gutter and sidewalk and repaved.