@Cathleen Ohannigan I am not sure if you found a solution to your dilemma.

My first property was my primary residence in Chicago, and I'm hoping to make another purchase by the end of the year.  

This means I am bringing the money, which is coming from a HELOC on my primary residence.  

Bigger spaces are easier to lease because I can afford to invest money into marketing or split a fee with a broker representing a tenant... however as these are a variety of small office and retail spaces, I'm looking for low-cost advertising solutions.  

not on a condo - they are not lendable, at least not in that price rangeThere are condos for $200-300K, these can be financed with conventional as primary residence, but these won't cash flowing.My examples are not on MLS - it's not retail price. 

BP crew,I plan on transitioning my personal residence SFH (3/2) into a rental within the next 6 months.

It was also the last year that I could sell and not pay capital gains because I had lived in it as a personal residence for 2 of the last 5 years. 

I sent three messages that were similar to three different people within 5 miles of my residence.

For instance cashing out 280k from my primary residence and use it as down payment to purchase a 700k investment property.Thanks,Jason

Another investor will see the value differently than someone occupying it as a primary residence, but it still carries value in both cases.