$40k is a great start, but hard to put a portion of it into work on a commercial level. 

I’ve thought about RE agent, or trying to find an entry level job in mortgage lending, or even workIng for someone doing rehabs and/or buy & hold would be awesome as this is what I aim to do as an investor myself.

You will need some level of training before diving in, and it usually takes a few months of preparing before you are ready to actually buy something.

Lower rent. 

If the assessment is lower than the principle amount due then the lien gets reduced to that amount.The assessment amount is due within 60 days.

All of the numbers I was using were "lender estimates" which I understand generally aim for erring higher rather than lower.

This creates two challenges for me:1) I'd like to do moderate to significant renovations on the units, and my business partner plans on owner-occupying one of the units, so we would need to permanently vacate one or, depending on the property, even all of the units. 2) In order to make the numbers work I'd need to dramatically increase rents (by several hundred dollars/month) to bring them up to market levels. 

Rent/price is lower here than you would expect listening to the podcast.

Just get it rezoned and level the house to your hearts desire.

The lower the Loan to Value (LTV) the lower your risk is.