Make some calls and shop around- not many banks do HELOCs on investment properties. 

That doesn't mean it's a bad idea though- just shop around and see if you can find a rate that will reduce your monthly payments.I think you should definitely do some serious saving before you buy the next property.

'Brooklyn' style growth is pushing west ie coffee shops, art galleries, creatives Upstate Craft Beer Co etc. 

Most renters (in my experience) are far more practical than homeowners, and want a place to be affordable, safe, clean and near where they work or shop. 

I am going to shop our local banks next week for lending on 20 properties at once.

@Laura WyzykowskiPer this NY Times article, the average American knows around 600 people.https://www.nytimes.com/2013/02/19/science/the-average-american-knows-how-many-people.html#:~:text=The%20average%20American%20knows%20about,do%20you%20know%20named%20Kevin%3FPer the US Census Bureau, the average American moves 11.7 time in their life, which based upon an approximate lifespan of 84 years, works out to be about every 7 years.https://www.census.gov/topics/population/migration/guidance/calculating-migration-expectancy.html#:~:text=Using%202007%20ACS%20data%2C%20it,one%20move%20per%20single%20yearSo, if the average American knows 600 people and they each move about every 7 years, that means that the average American knows around 85 people that move in any given year.How many of those moves do you want to be involved in?

Should I shop around?

Russell, a while back you recommended Christian Oropeza for landlord insurance policy who has since opened his own shop and he has been fantastic to work with! 

There are a few in Wicker Park, but not the area I was looking at specifically.It’s more residential but walking distance to the shops/restaurants on Division.

Shop around and talk to a few PM's and see who fits what you're trying to accomplish.As for what you need to do to get your unit ready, you should have known this going in.