-The mention of syndication being less risky than HML...I'd suggest it is more risk, possibly much much more since you don't know whether you are good or bad at vetting the operator right now.

Mostly due to the fact my spouse and I agreed on her to have zero involvment in any sort of RE investing (and its our home) I think once you have a good 6-12 months of reserve cash (operating expenses for your own life saved as a back up incase things go bad) save enough liquidity to get the ball rolling on your first invesment.

Rarely do they like such units being operated in such way.

And having some operating income is ideal but not necessary if I expand through HELOC and refinances.

In my opinion, even if you partner with a local PM company or turnkey operator your returns will drop significantly.

Partner up with money partners and you be the operator.

On a more enterprise scale, I employ RevMax software as well as a fractional revenue manager who looks at the prices daily on a market level and a comp set level. 

@Kyle Kulhanek To retitle your Chicago condo into an LLC for liability protection, start by forming the LLC with a clear operating agreement outlining ownership and responsibilities.

Both my wife and my background is in manufacturing, specifically operations, customer service, and project/account management. 

We can still choose how much to pay someone to operate it if necessary.