The problem is this, if the roof is too old or has trees around it.

My solution was to call a landlord in the area to get those accurate rent rates.For me, starting out, I'm focused on big goals and doing it right.

Wetlands, huge trees, erosion problems, neighbors lot filled with trash, etc. 

If exterior is in bad shape and roof, windows, parking lot, main water line, tree root issues pop up that could add thousands per door to the property.When you use high debt service on vacant properties you want a fast lease up.

However plant replacement depends trees or plants?

I know getting investors is the obvious solution but the people I know I feel like don't have money or want to invest with me because it's my first deal and I am not proven yet. 

I feel like I'm barking up the wrong tree because this definitely needs a lot of repairs.

And note that your strategy/solution will depend on how much equity they have.

It seems the 99% safe solution would be to use property management.

@Taylor Jennings  Scenario 1: looks like the easiest solution and the least stressful.