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!).

A friend of mine who is also a real estate investor told me that having a kid under 6 year old will bring only troubles with sec 8 as they regulate the building codes way more strictly and can ask me to repair "unnecessary" things. 

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

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?

I’m just trying to figure if it makes sense to delay the closing to 2019 but my question I mentioned above re: the date of election after starting the flip project is whether or not it would prevent me from getting taxed as S Corp on profits from that certain project because the election would be made after the project started?

Fannie has/d a deed restriction on their homes that prevented a lot of buyers from flipping them as-is.