9-unit Under Contract in Chicago...Ideas?

[Edouard Pierre]

Hi BPers! 

To keep a long story short I'll get to the point. I'm under contract on a 9-unit building in Chicago. Found it off-market and it's an estate sale. It's a corner building next door to a 7-unit building I acquired last year...it couldn't have worked out better in my opinion (I'm a broker and was asked to list it so of course I bought it cheap..the luck!). It's been mismanaged for a while and there are 4 units out of the 9 that are occupied. Rents are under market value at the moment and all but 1 tenant are current on their rents. 

I'm aware that "re-training" (as @Brandon Turner would say) will be part of the work involved in getting this property churning at full efficiency, however I think I have more important decisions to make (see below). 

As we are doing our due diligence (FOIA, Estoppels, etc...) I'm getting contractors lined up to get estimates for the rehab. My experience rehabbing the next door 7-unit building wasn't terrible, however it was done in the timely manner I had expected. 

MAIN QUESTION (1 & 2):

1) Besides due-diligence...what would your first moves be in establishing yourselves as the new owner (learned not introduce myself as the owner but rather property manager)? What would be your advice on increasing the rents (5yr+ tenants and very under market)? 

2) This building is being heated by 1 big gas boiler and is relatively new. Bill is on a budget plan and cost $1500/month year-round ($166.66/unit). Installing individual high-efficiency furnaces including ducting would cost around $5,000 per unit and result in me not having to pay the bill year-round. Doing the math isn't that difficult in terms of return on investment but the biggest question in my mind is...is it worth it? This is a C-class property and heat included is sought after. I'm unable to come to a conclusion on whether it would be more financially advantageous to keep what's there since it's not broken and increase the rents accordingly rather than add on such a project. To give a little more perspective:

Each unit would rent for:

$900 = individual furnaces

$975-1025 = keep boiled/heat included 

I assume most will need more information on the building and its financials to really advise...ANY advice is a huge help. Thank you!!!!