Everything is doable. But it will not be a trip for people travelling on a budget.
Some fares:
Lucerne - Titlis and back: 130 USD
Luzern - Pilatus and back: 105 USD
Interlaken - Jungfraujoch and back: 205 USD
Interlaken - Schilthorn and back: 135 USD
Zermatt - Gornergrat and back: 90 USD
Zermatt - Kleinmatterhorn and back: 100 USD
You can get some discounts with the Swiss Pass and with the Swiss Half Fare Card:
http://www.swisstravelsystem.ch/en/content/offer/tickets/
http://www.swisstravelsystem.ch/fileadmin/pdf/STS-GB-M-11-EN-WEB.pdf
You plan to visit 3 Swiss towns. Lucerne, Geneva and Zurich (the other places you mention are holiday resorts with no historic buidlings, museums, etc, except Chillon castle). I suppose you know that there are more interesting towns in Switzerland than these 3.
Now to your questions:
Pilatus in half a day is possible. My sugestion:
Leave Lucerne city center by bus at 8.15, change at Kriens to the cableway and arrive at Pilatus at 9.21. Enjoy the panorama. Leave Pilatus at 10.50 by cog railway up to Alpnachstad, change there to the Lake Lucerne boat and arrive at Lucerne at 13.11. You may leave the boat 10 minutes earlier at the Transport museum pier and visit the Transport Museum in the afternoon.
Which Lake Brienz Dinner cruise? 1 boat leaves Interlaken at 16.25 and comes back at 18.50 (wekends from mid June, daily in July and August), another one cruises between 19.00 and 21.15 (saturdays from July 9th to August 21st only).
Harder is close to Interlaken: 10 min by cablecar.
The Trummelbach Falls are of easy reach from Lauterbrunnen, between Interlaken and Jungfraujoch.
Chillon castle is a 5 minutes train, boat or citybus ride from Montreux. There is also a promenade (nice walk) along the shore of Lake Geneva.
Geneva has some good museums. If you don't get lost there, you can easily visit the town in one day. You don't need any guide.
You could also go back to Montreux by boat:
Geneva Eaux Vives dp 15.00 - Montreux ar 19.23, or
Geneva dp by train 17.36 up to Nyon, then boat Nyon dp 18.27 - Lausanne ar 20.20. Lausanne - Montreux by train (20 minutes, 3 trains every hour until midnight).
The chocolate train excursion to Gruyeres and Broc takes the whole day. Chillon castle would be closed when you come back to Montreux.
Zermatt: Gornergrat is as good as Kleinmatterhorn. But it's not forbidden to do both (if the weather is fine, otherwise it wouldn't be worth the money).
Zermatt - Rheinfall: take any train leaving Zermatt between 7.39 and 18.39 (departures every hour), change at Visp and Winterthur; 4 1/2 hrs later you will arrive at Neuhausen am Rheinfall.
Swiss timetable: http://www.sbb.ch/en/index.htm