Sell, Cash Out Equity, or Refi & Leverage?

[Claudia Del Leola]

I have 3 BR 1BA condo in Chicago's trendy Logan Square neighborhood (currently cash flowing $350/mo). I am debating some options in order to make the jump into a multi unit investment.

CASH OUT EQUITY: 

I should be able to refi into a 30 yr, cash out $107k, and cash flow $1000/mo. 

REFI BALANCE OF LOAN:

I could refi into a 30 year, cash flow $1,000/mo, and take out a separate $250k commercial loan for a multi unit investment. Cost of loan $1425/mo

SELL & USE TOWARDS MULTIFAMILY:

I could also sell, net roughly $150k, put together with another $50k cash and use towards a multi family investment. I would lose the $1000/mo in cash flow, but not have any additional liabilities.

I am really racking my brain here, and am ready to hear from all of you who have been there before contemplating, your "1st big deal." I think I know what I want to do here, but want to get some insight to make sure I haven't missed anything.

Please let me know your thoughts, experience, and other options I haven't considered.

Thanks in advance for the help!