Reuben and Mandy Visit New York

The idea behind this card is that the ridiculously dressed country bumpkins are so overwhelmed by the tall buildings in New York City that all they can do is look up. The name Reuben is not a coincidence either. The nickname for Reuben is Rube. Here's the definition from Merriam Webster:
Rube

Pronunciation: \ˈrüb\

Function: noun

Etymology: Rube, nickname for Reuben

Date: 1891

1 : an awkward unsophisticated person : rustic
2 : a naive or inexperienced person

This card is greatly enhanced by the message. The sender, undoubtedly a country bumpkin himself, seems to have relished the humor. Here's the message side of the card:

The message sent to Miss Alta Bonney in 1908, reads:

We are nearly through haying would have got done if it had not rained this week. from your friend Charlie

Madison Square, New York

Here we are at Broadway and 5th at Madison Square in New York City.  The 5th Avenue Hotel, shown on the left on both cards, had one of the world's first elevators. The cards are both prior to 1907. The first one is from 1906, since the company only printed cards in 1906 and 1907, and a 1907 card  would have had a back divided into two sections for address and message.
The 5th Avenue Hotel, built in 1859 at 200 Fifth Avenue, was demolished in 1908. The site is currently occupied by the Toy Center Building, built in 1909.

On the second card, you can still see the Fifth Ave. Hotel on the left, but you can also see the tower from Madison Square Garden off on the right. Madison Square Garden was designed by Stanford White, who was also murdered there in 1906, about the time this postcard was published. White was murdered by millionaire, Harry Kendall Thaw, over White's affair with Thaw's actress wife Evelyn Nesbitt.

Here are the backs of the cards in the same order as above:

Streetcar Sundays - Pittsburgh, Pennsyvania

This card shows downtown Pittsburgh at the turn of the century. You can see the streetcar tracks and what looks to be a streetcar down the line.  On July 4, 1897 there was a serious streetcar accident in Pittsburgh.  This excerpt is from GenDisasters, a website that chronicles the disasters that shaped our ancestors' lives. Warning: it is a little graphic. I am also puzzled by their willingness to predict who will die.

Streetcar Wreck on an Incline at Pittsburg.

PITTSBURG, July 7. -- Four people were fatally injured and 18 or 20 others were more or less injured in a streetcar wreck on the Forbes street line of the Consolidated Traction company last night.  The names of the seriously injured are:
Michael Doyle, motorman, top of head torn away, two ribs and a leg broken; will die.
W. A. Manly, employed in the circulating department of The Times, scalp laid bare and hurt internally; probably die.
Miss Smith, skull fractured; will die.
C. C. Rogers, leg and arm broken and hurt internally; will die
Mrs. Mary H. Wilson, Allegheny, two ribs, right leg and left ankle broken; may recover.
The full list of injured is not ascertainable.
The wreck occurred on the Soho hill at the time when the immense crowds which attended the fireworks display at Schenley Park were returning home.
An Atwood streetcar had gone about half way down the hill when it jumped the track, closely following it came an open summer car with a trailer, both densely packed with people.  Before the second train could be stopped it crashed into the derailed car. Hardly had the first collision happened before a third car, heavily laden, came down the hill at full speed and forced its way into the wreck ahead.  It was the second crash that did most of the damage and the scene was indescribable.
Fort Wayne News, Fort Wayne, In 7 Jul 1897

I'm not going to go into the details of Pittsburgh's illustrious streetcar history, in part because there are a few existing web pages that do a very nice job of it. One is an article written in 2006 by Matthew Campbell for Carnegie Mellon's student newspaper. Here's the link: Streetcars define Pittsburgh's transportation history. And then of course, there's Wikipedia, which also has an impressive amount of information.