(NOTE: The buyer base for this area could be another investor, but more than likely it would be someone looking for a ski/2nd home.)While I can't account for everyone and am currently of the mindset that I will meter all "units" (pending any influential feedback here in the forums), I'm curious if anyone has any thoughts on pro's and con's to metering everything into 4 units or just metering each legal side (into 2 units) and splitting the upper and lower utility payments based on some other criteria (e.g. square footage).

You should consider utilizing a DST or two as a backup for your exchange if things don't materialize in time for your exchange. 

How big is the loan you are going to to take of the extension?

Id try to 3-4 months covered  just for the analytical side, can always lower reserves ... other than that are tenants paying all utilities?

@Joe DavisMy tenants pay all utilities, in my single family.

The separate utilities are going to be easier to deal with unless you plan on having other unit not have to pay for their utilities.

I would now like to try to collect unpaid utility bills and damages from a tenant, but I do not know where to start.Here's where I stand...The tenant moved out on July 31 leaving unpaid utility bills and damages of $723.29 (in addition to his security deposit).

At some point in the paperwork process you’ll have to report anything/everything the owner pays for and everything the tenant pays for (i.e. rent, utilities, trash, other, etc), and sign a Landlord Certification form that says (among other things) that you “understand that the tenant’s portion of the contract rent is determined by the Housing Authority and that it is illegal to charge any additional amounts which have not been specifically approved by the Housing Authority.”So you just have to report it up front.

If you have a self-directed IRA you could utilize those funds or you can joint venture with an experienced note investor. 

In addition to that i've created a pretty automated sales process for investors to utilize & am always available when you have a specific property of interest.