The window well is supposed to drain down to the foundation and drain tile system.

You can install gutter extensions to force the water farther away from the foundation.If these simple steps do not fix the issue, it may be necessarily to install drain tile and a sump pit to collect the water.

. - Order 10% more tile than needed!

The sad thing is the PM company didn't even have a recommendation and the condo association pays heat so they should hook up with a supplier/installer.

I manage these properties for the owners and if it was my choice, I would rip carpet out of all my houses and put down tile.   

Realitve to comps in the area, the house is completely remodeled (stainless steel appliances, granite countertops, Italian tile bathroom, new hardwood floors throughout, high-end light and plumbing fixtures, etc). 

I will need to replace the carpet in the entire upstairs (downstairs is tiled) and I would like to install vinyl instead upstairs.

Obviously a full kitchen remodel doesn't make sense at this budget, but the house needs quite a lot:- New roof- New windows- New bathrooms (currently it's set up as a 3/1, but I think adding a second bathroom would be a big add)- Flooring is okay, but the tile is dated- New front door? 

Considering I was told that I could remove asbestos tile on my own on anything less than a 4-unit, it makes me think the city doesn't care about much.

I had another skilled handyman (Specializes in tile, but does other stuff as well) do the rest.A simple bathroom for a rental property should cost you around $5k-$7k in SE or MW.