Could easily save you thousands and prevent you from into a bad deal that costs you time and money.

I felt like a lot of time and gas had been wasted walking through these properties.I have another idea to prevent wasting time/money, that I think may be better but I'd like some opinions on it...Would it be a bad idea to make offers based off of photos/virtual tours, if said offer gets accepted, use my inspection period to walk through and either go through with it or back out?

I used to wait on the sidewalks till near the end to prevent damage but I hated seeing moms with strollers trying to traverse the busted up old sidewalk or dirt and chunks of rock.

Allowing the soils to drain is the proper fix to prevent the pressure.

@Allan Calderon Run it until it dies or becomes noticeable...some might not agree with that, but I want to get all the life I can out of everything that I can where it is not causing an immediate issue...this frees up cash for preventative maintenance and repairs. 

It will cost you in the beginning but it will save you in the long run (an ounce of prevention, worth pound of cure!).

Would the tax issue prevent me from doing a cash-out refinance with a lender?

We've even had tenants moving tell us that there friend who is moving in is taking the couch, we make them move it into the front yard so their friend can see an empty house and then the new guys will have to move it back in.I would skip furniture personally, sure you can buy it cheap but the kids I rent to don't want to hang out on a couch with somebody else's DNA all over it, or Pizza stains or beer you get the idea.

Ideally I want to be there for a year or two then move out and continue renting each dwelling unit.I am wondering if there is anything legally that would prevent me from doing this without going through the process of making it a legal duplex?

Either strip the upper treads then stain/poly both sets or prime/paint both sets black.