Potential duplex to fourplex conversion

[James S.]

After lots of searching for my first property, I've come across an interesting one. It is technically a 2-unit that can potentially be converted to a 4-unit. The original structure has near identical up/down spaces that were originally separate units. A previous owner extended the house to have two near identical (to each other) more modernized units up/down towards the back of the structure. It operated illegally as a 4-family before getting notice from the town that it was legally a 2-family. The very surprised current owners converted it back to 2, though I don't know exactly what that entailed.  In its current form, the back of the house is rented and the front unoccupied.

This presents an interesting opportunity, but also several challenges: 

• Front units need updating, and front of building is over 100 years old
• Front units have no stoves/ovens (they once did and were pulled, no visible gas hookups)
• Front units heated by gas, rear by electric
• Some units share utilities, not yet clear which units or utilities
• Zoned as a two-family, like most on the block, though there is a 4 or 6-unit building across the street on a larger lot

This is an ambitious project for someone with my lack of experience, but I would like to explore it further before ruling it out, as I see the potential for considerable forced appreciation and solid cash flow.  It is also part of a community typically known for extremely high end homes and good historical appreciation.

I am very analytical and detail oriented, so I'm somewhat comfortable researching specific questions as they come up, but I need some direction on the big picture.  How would you suggest I approach finding out what needs to be done to convert this to a legal 4-unit, whether the town will allow it at all, what work needs to be done (including separating utilities), and at what cost?  Can I also assume conventional loans are out of the question? If the property is off market and the owners are moving slowly, can I do most of this analysis before making an offer?  Big question, so thanks in advance.