Based on current prices, SFR will maybe get you $100-200 positive (best case) and worst case break even.

You have to document your intent to defend your position. 

Would you ever consider purchasing a house hack that has a small amount of negative cash flow (when considering all expenses to budget for, of course), knowing that cash flow would be positive once you moved out and gained income from the unit that you were occupying?

While the home will still technically produce negative cashflow, it would give me a very cheap monthly payment on a house that is steadily gaining value.Now, over the next year, my goal is to purchase another SHF in the area as my first official "rental" property, with the intent of positive cashflow and passive monthly income.

I don't do the due diligence unless I get a positive response from the property owner.  

I may have left out insurance, but the amount is so low it will impact the bottom line/decision very little.3. 

Is a property with that much needed repair work maybe too large to tackle for a beginner in my position?

It would need to be in the range of $3000 - $3500 to produce positive cash flow as well as cover your equity value. 

They should take effect at the start of 2019 but not positive.

I'm sure you've got a lot on your mind, but if you'd like to connect with a few event planners to talk about what they're looking for (should impact/influence your build-out) let me know and I'll send you a couple names.