To read a hint, or how to solve, or the solution to a puzzle, click on the link. If you still don’t have it, feel free to look at more links or read the “how to solve it” section.
STEP 1: (Newspaper)

Hint 1

In order to know the first place to travel, it’s a personal clue that you must unravel.

Hint 2

When this tricky puzzle is making you vexed, ad every fourth word for where to go next.

How to solve it

Look in the newspaper, particularly the personal ads. One of them will tell you what do do next.

Solution

One of the personal ads on the back page is titled “Waiter’s Secret”.  If you read every fourth word on each line, it reads, “Mad, hat, tan, Room, Hotel, Pennsylvania”.
STEP 2: (Phone book page)

Hint 1

If finding the number seems an order that’s tall, use the letters and numbers to make the right call.

Hint 2

The dial of your phone will show you the key to how letters and numbers work in harmony.

How to solve it

Look for the name “Madhatten Room, Hotel Pennsylvania”. When you find it, determine what the letters and numbers mean.

Solution

The phone book page contains a telephone number to call. The number listed for the Madhattan Room at Hotel Pennsylvania is DI amond 5-1414. This is an old fashioned way of writing a phone number that utilizes the letters of the alphabet found under the numbers on a standard phone keypad. If you use the number address ‘412’ as the modern area code, the number is (412) 345-1414.  The message says “Hello.  Thank you for calling the Madhattan Room at Hotel Pennsylvania. We cater to the discerning patron and our staff is here to serve you the finest food New York City has to offer. How may I help you?  ———-A table for tonight?  Of course.  How many will be in your party? ——-Very good.  Your reservation is set for 8 o’clock tonight and our Maître D, Jacques will seat you at our premier Jack Kreindler table for top shelf service. Be sure to order our signature appetizer the “John Barleycorn” for a special treat!  We look forward to seeing you this evening.  Goodbye.”
This is a clue to now open the envelope addressed to “Jacques”.
JACQUES’ ENVELOPE:

The Napkin - Hint 1

When you find yourself stuck where it’s high and dry, the napkin will show you the word to try.

The Napkin - Hint 2

The napkin holds mysteries, this much is true, but when you look close, the picture’s the clue.

The Napkin - Hint 3

Part of this word is what you’d find on a hen.  It’s also the name of a movie with four funny men.

How to Solve It - The Napkin

There is something about the imagery on the cocktail napkin. There is a clue in the movie listings in the newspaper.

Solution - The Napkin

The napkin contains a picture of a horse and feathers. Also the newspaper contains an ad for the 1932 Marx Brothers movie, “Horsefeathers”.  However, what this means is yet to be revealed.

The Coaster - Hint 1

When solving a cipher your focus must be – an unwavering appetite for finding the key.

The Coaster - Hint 2

The wheel seems random, there is no doubt, but a random quote helps figure it out.

How to Solve It - The Coaster

To figure out what the coaster is for there is a clue in the newspaper personal ads. The encrypted message is written somewhere in the mission. The key is a celebrity.

Solution - The Coaster

One of the personal ads in the newspaper describes a “pangram” – a sentence that uses all letters of the alphabet.  The quotes on the Table Reservation Cards are all pangrams.  One of them is the key for the cipher wheel.  The quote to be used is the Charlie Berns quote.  If you noticed, the phone message said to ask for the Jack Kreindler table, and the biography card for Berns reveals him to be Kreindler’s partner.  Write the quote, “Pack my box with five dozen liquor jugs”, into the empty spaces on the coaster starting with the space next to ‘A’.  The wheel is then used to decipher the encrypted message on the poster that says “NEXXH PCOVCIJ EO MDJ BJH MC MRJTMH CTJ PVGQ JTMKH”.  The message reads, “JIMMY COSLOVE IS THE KEY TO TWENTY ONE CLUB ENTRY”.  This is a trigger to open the “Jimmy Coslove” envelope.
JIMMY COSLOVE’S ENVELOPE:

Hint 1

When it comes to high fashion it pays to perceive the hidden message you can receive.

Hint 2

Bundle up with your scarf for winter is here, but first, find the message that may be unclear.

Jimmy Coslove - How to Solve it

Look closely at the scarf. There’s a message there that will lead you somewhere else.  Once there, however, you may find yourself stuck high and dry.

Solution

If you use all the numbers, words and letters that appear on the scarf you will get a website URL:  “https://theresystance.com/21tellittosweeney/”.  The password is from the cocktail napkin – “horsefeathers”.