"First, I'm looking for suggestions to visit/see between Cologne as we drive to Oberwesel."
North of Koblenz: Remagen is a small, attractive town and home of the WW II "Bridge at Remagen" Peace Museum - which chronicles the battle for the bridge.
Across the river from Remagen is Linz am Rhein, an even more attractive old world town.
A car/passenger ferry connects Remagen and Linz. Maybe see Linz first, cross the river once to see Remagen, then head south to Oberwesel. Alternatively, you may want do fit in one more important sight that first day - Marksburg Castle in Braubach - and the reverse order would work better (see Marksburg below.)
The other worthwhile sights along the Rhine IMO are generally south of Koblenz and near enough Oberwesel that you can see them easily from there.
Boats: The best part to cruise is Bingen-St. Goar, or Bingen-Boppard. For a half-day outing, you might take the train to Bingen, cruise north to St. Goar (1.5 hours,) see Rheinfels Castle there hike briefly along the cliffside to the Loreleyblick lookout, then train back to Oberwesel (5 minutes.) For a FULL day, add a 2.5-hour hike (see below) and walk into Oberwesel. ALTERNATIVELY... for a FULLER day, start with the cruise again - from Bingen north to Boppard (2.3 hours,) do the chairlift ride and a hike around up there. Lunch at Gedeonseck? See Boppard. Train south to St. Goar (12 min.) for Rheinfels, train back to Oberwesel
Hiking: Rhine Castle Trail on the Oberwesel side is great - hike between Oberwesel and St. Goar offers terrific views and varied terrain.
East river bank: Marksburg Castle in Braubach is excellent. If you can get there by 4 pm or so after Linz and Remagen on Day 1, take a tour on the way south to Oberwesel. If not, pick a day and drive there (use any ferry crossing) or do a train-to-St. Goar (5 min.) + ferry to St. Goarshausen + train to Braubach (20 min.) journey. Also on the east bank is a summer bobsled run near the Loreley (drive up or use shuttle bus from St. Goarshausen.) Rüdesheim to the south may interest you as well but be advised it's tourist central.
You can do all or some of these 4 days by train as Lee suggests. Of course the cruise day requires a train. The VRM day pass you mention works great for outings from Oberwesel north. If you use the train to head south from Oberwesel to Bacharach, Bingen, or Rüdesheim, the Rheinland-Pfalz ticket is your friend. (Note that it also covers the VRM area.) Buy these day passes at the station ticket machine.
Eltz Castle and Cochem are excellent choices as well. Note that there's a waterpark in Cochem and in nearby Klotten an amusement park as well that gets GREAT reviews.
http://www.klotti.de/en/