@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?

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.

Your best payback is actually sealing existing windows to prevent drafts rather than replacing.

As much as I hate the smell of cigarettes, I dont think there’s any way to prevent tenants from smoking. 

They think that asset protection planning is immoral because it prevents a creditor from collecting on a judgment entered by a court. 

@Ned Carey How exactly can we do an addendum correctly and what to avoid/prevent that makes it incorrect?