There is a precaution many folks forget or are not aware of when using house wrap on older houses---those build before the mid 1900's.

Many of those houses had little planning for moving fresh air into and stale air out of the structure, other than the normal leakage by windows/doors/etc. When such a house is wrapped, there is no way to get air movement and the house air becomes stagnant and can cause sick building problems.

It is easy enough to add an air exchanger to a central air unit to prevent that from happening.

I installed a lot of vinyl siding in years past, but would look at the newer siding products now on the market. Vinyl would not be my first or second choice today in a cold climate.

Cement board(Hardi products is one brand) is durable in cold weather. And there are steel siding and faux stone products available.

I have a house now with a combination of insulated steel lap siding and insulated faux cedar shake shingle plastic siding. Zero maintenance(except washing) and the siding is several decades old.

insulated vinyl siding isn't in direct contact
and does little to add insulation value.

I too perfer hardi to vinyl. just don't like
the looks of vinyl.

houses are leakier than you think. we make
walls fairly tight, but it is the holes in
the ceilings to attic that are the main
contributors to air leakage.

if you are worried have a blower door test
to determine air changes per hour.
below .30 air changes requires fresh air
per ashrae 62.2 standare.

in existing homes we hardly ever have to
add fresh air. new construction..is a different
story.

best of luck