In fact, I suspect they are responsible for a good portion of the rent/value increases we've seen over the past decade, since nothing really hits the public market. 

I am wondering if I can ask my realtor to do comps for me for those houses even though I do not intend to buy the properties through the realtor because the landlord will increase the prices if we go through the realtor. 

It has also increased in value by 20%; therefore cost basis has reduced and capital gains exist.I clearly understand I need to pay transfer tax.

The bad side is that homes are very expensive there (I'm from Arlington and have seen the increase in prices).Also, it is my opinion that you are better off having a 2nd house rented out and having someone help you than if you didn't.

The ultimate plan is to get the HELOC and Increase the equity to 25% to make it an investment property but that will take an additional 45 days.

At a 5% downpayment, the monthly total payment is ~5k and perhaps the rents could be increased a bit but even then, they'd only be around 5k total monthly gross rental income..after any expenses and repairs you're in negative territory. i don't really understand who would buy that property..I guess an owner occupant who doesn't mind having a higher personal monthly payment still, or someone just seriously banking on appreciation and willing to incur negatives during the meantime which seems silly..but i agree with the original poster that lots of multis in these areas (wicker/logan proper/humboldt) are priced like this kedzie one and basically aren't a good deal sadly, since they are the nicer properties (location and often turnkey wise). have to go further north/west to get the deals. im hunting for a 2-4 flat myself and wish it could be in prime palmer square location like the kedzie unit linked, but the numbers just dont work

It may continue to increase over the next two years and you’ll be kicking yourself that you didn’t do it sooner.  

Job growth is a sign of a solidification of market dynamics as well as an increase in per capita income.

If one does give you their access they'd be risking a violation, and subsequently, their license.

I guess I would self-manage and basically just not count any of my managing as an expense when reporting my business taxes (thus increasing my total taxable income but not having to pay SS/Med tax)But then what happens if I don't pay a med/ss tax for the next 40 years of my life?