These are two very different goals with different activities required to achieve each.

After one year of improvements, new tenants, raising rent, and a ton of "sweat equity" I Refinanced to achieve 30% equity, got rid of my PMI, balanced out income to mortgage payments.

It will be easier to achieve living for free, and it will help you scale you portfolio quicker.

That would definitely decrease the cash bleeding, but it seems like I will not be able to achieve positive cash flow if I refi remaining balance to 30 years under current market climate, unless the rent goes back up to $2000.

Finding a job with good income will make it easier to transition to real estate investing, eventually achieving sufficient cash flow and financial freedom.

Hence, two syndicators can look at the same deal and share similar assumptions when it comes to putsches price, rent, expense increases and even premiums (the increase in rents achieved by implementing a value-add plan – rehabbing the property and renovating the units).

If not, real estate is just one way of achieving passive income.

It seems like you have some good goals set for yourself and the connections you make on here will definitely be able to help achieve them.

There are various areas to choose from to live in the Denver metro area and the prices can vary greatly so it would be best to understand the lifestyle you want to achieve. 

This can be useful for managing assets and/or achieving greater anonymity.