They all generally seem to be negative cash flow about 99% of the time.

It's a strong cash flow market.

Also, I have about $8k in cash and no debt at all! 

Seems to be a really smart place to park cash at 6% Cap rate, with depreciation tax benefits and projected equity increases in the 23-30% range in the next 3 years.

For example, if you’re a first-time buyer wanting to see 3 different cities, low down payment Ioan, no real idea of what you’re looking for, and need to lose 3+ offers before you’ll listen to my professional opinion on offer price & terms, you’re going to be paying me a lot more than an informed cash buyer looking in a specific neighborhood that listens to my advice so we quickly win the bidding wars we still have with lack of inventory in desirable neighborhoods.

As for renting, going cash flow negative isn't great, and your home isn't likely to appreciate as fast as it would if it was a single family home, so holding with hopes of increasing appreciation may be a verrrry slow play, but if you can afford to hold, having a tenant pay down your mortgage is an additional great benefit to real estate investing. 

Purchase price: $580,000 Cash invested: $75,000 Townhome in the highly desierd Rosemont area.

I think the majority of the confusion likely comes from the fact that most all of the builders that have inventory on our marketplace are offering unique incentives like extensive rate buy downs, free PM & maintenance guarantees, up to 10% price reductions or up to 10% cash back, etc. 

Is there any potential for doing a cash-out refinance on the duplex and using those funds for the purpose of buying the property you want? 

You are paying taxes on the gain, not the cash received.