It is possible that if you have a concrete drive way its is not sloped down toward the sidewalk so that rain water will run off.

Have seen several in my area that spill on or near sidewalks.

Also, you need to have some kind of maintenance plan (roof/furnaces/bathroom floors/concrete sidewalks etc.)What are the terms of your loan, what percentage are you putting down?  

He dug from the house to the sidewalk.

@Kyle Hipp I don't think I would charge a tenant to damage coming from the outside of the unit, especially if the window is facing a public area like a sidewalk or street.

One thing for those who are not familiar with the situation in CA OR  and WA. and Honolulu  the govmit has no backbone.. they just allow the homeless to pitch tents right on the sidewalks of the down town areas or under freeways or dead end streets they just don't up hold the laws on vagrancy.. this gets out in the community ..

The city required us to repair sidewalks, another $5k.

We plan to paint, put on new shutters, remove the fence and shrubs at the sidewalk, remove the pachysandra at the driveway and clean up the landscaping.

With the rains this past week, I was able to identify where there was standing water for an hour or so after the storm passed, so I suspect the grading of the sidewalk running along the house is the main source of the problem.Does anyone have a recommendation for someone that can address our drainage/moisture issues, and ideally also do whatever treating is necessary on the interior?

I can't charge my tenant because I failed to fix the uneven sidewalk or failed to maintain the gutters.