I am actually pretty open to all of  your mentioned criteria, except the the first...1.

The option of selling now and waiting to buy might be a solid option except you will not be able to do a 1031 exchange, which may not be a problem since you have lived in the property for 2 years.

Except for one problem... 

As far as I can tell I've got identical coverage on every property.I talked to my contractor ,who has built houses from scratch, what it would cost to rebuild these in the event of a total loss situation and he said that $200,000 is the max on all of them except the all brick 1750 sqft one...which would be closer to $250,000. 

Washer & Dryer is the exception to the "big" appliances that I provide.

They provide a chart, based on their experience, that gives you per-square-foot costs for each combination (except anything to do with "Custom," since, by definition, it's custom and can't be ballparked).Based on their chart and my (admittedly subjective) ratings of "Standard" finish level and "Remodel" scope-of-work, costs should be roughly $25/sf.

One exception is the Illinois Fair Plan.

In most SFH rentals the tenant will pay for all utilities except, possibly, trash pick up (the cost of such is often added to the owners yearly tax bill).As others have mentioned, in multifamily units there may be only one meter for the entire property (and splitting this into individual meters is cost prohibitive for the owner). 

We always agree before we purchase anything, except for one foreclosure that I bought online, but he wasn't mad when we made $37k.

—The doctrine of the right of survivorship in cases of real estate and personal property held by joint tenants shall not prevail in this state; that is to say, except in cases of estates by entirety, a devise, transfer or conveyance heretofore or hereafter made to two or more shall create a tenancy in common, unless the instrument creating the estate shall expressly provide for the right of survivorship; and in cases of estates by entirety, the tenants, upon dissolution of marriage, shall become tenants in common.History.