Without accounting for management fees (I have not yet decided if I will try to self manage), and with planning to raise rents to typical market of $825 for each of the smaller units, and $1200 for the larger unit, does this seem like a worthy first investment? 

Where do you plan to invest?  

I feel I have a rough idea, which is..I'm in Rogers Park, my next important step is to wait out 1.5 years until I can fully rent out the condo, but for the meanwhile get a roommate to save more money.

Speaking with a lender is a good plan, they can help you plan for the future.  

I’ve also thought of plans for a smaller scale venue too.

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The plan is to use the heloc to purchase additional properties, and basically brrrr and pay back the balance - then repeat.What I didn't realize is how difficult it is to find a business heloc.  

I think by waiting to last minute to put things together you miss items and year end tax planning becomes problematic.

I would imagine most attorneys located around the MA, NH border area plan to make more than $200,000 per year.

For down payment, plan to need 30-40%.