I have been looking a lot into purchasing a portfolio rather than buying each property individually.  

As individual taxpayers - we run on a cash-basis method of accounting.Waiving rent means that we never collected the rent. 

I can not guess what score any individual may have therefor reject any applicant that does not have a score.One principal I have always operated on is to never work to try and make a applicant acceptable.

To be honest I'm not very familiar with TurboTax, but if answering Yes to that question automatically generates a Schedule E for that property, you should answer it No. 

I ended up on bigger pockets when searching for an online community of like minded individuals whose passion is real estate investing (so glad I found this site). 

Renting out a $1M property once you leave it is not going to generate any cash flow for you.Take your $300k and invest it in rental properties out of state and use that cash flow to pay for your rent or to quit working your day job and move someone cheap!

Check with your tax professional about your individual situation and nature of your expenses.

The section 8 individual sent me her application back first.I have already called HUD and am waiting for inspection.My question is- can i send the lease to be signed by the non-section 8 person or do i need to run the entire section 8 process because I received her application first?

If you're doing a bunch of flips, the income you generate will be taxed as ordinary at your marginal rate (unless done out of a c-corp). 

Zillow has always been one of those "too good to be true" for me in terms of lead generation because if it were that easy, why are over 90% of agents still failing within 1-2 years of starting?