Buying my first cruiser. I need help!
 

My advice is to go and ride both. You may find they ride the same or one may tell you it is the one or you may hate both. A Murray is a Murray and my guess you will love it or not. Bikes are cars and cannot really be bought without a test ride. Roger

i agree. all other things being equal as you stated, there may be a maintenance/build difference that you'd only notice from an actual ride.

being the hoarder i am, at $60 together i might buy both. mix and match to have one really good bike, a bike to ride and a bike for learning maintenance, a guest bike. an excuse to buy both shouldn't be that hard (for me at least).

You need to have 10 posts before you can post pictures. You are almost there. Again go ride the bikes. Roger

If you only plan on riding these a few times a year then ok. If you plan to ride regularly these are cheaply made and won't hold up to use. Personally I would find something built before WWII. A decent, base level woman's bike could be had for $200 plus a service and would last forever. It might not be shiny and pretty but it would have character! If you really want to step up get one of these--this is my '37 Elgin Skylark. V/r Shawn

https://cimg7.ibsrv.net/gimg/bikefor...09cbd02939.jpg

My wife rides a titanium Seven bike that cost more than $5000. For knocking around town she rides a Huffy version of the top bike of your 2 Monterys. Bought it for $25 and just add air to the tires once a year or so. Roger

I see a bit of a conflict. You seem to want a cruiser because it looks "charming", but want something you feel secure on. That can be two different things ...

Back before the 1990's some bikes could be quite heavy and often relied on only rear wheel braking. Somewhere around the '90s some MFGs started to make cruiser styled bikes with aluminum frames, braking on both ends, options for racks, etc. Bikes like the Townie

Feeling secure can come down to fit and features. Maybe go shopping for new bikes and see what I'm saying. Look at features and see what is recommended for fit size, appropriate saddle, etc. Then go back and look at what is for sale locally that matches what you have discovered works for you ...

If I had to chose I'd go with the top bike. Unless your doing some crazy riding a rear coaster brake is just fine. V/r Shawn

As you know Shawn I have often had to choose a bike based solely on pictures and the poster's description. The OP should go check them out in person, there is no magic thing that tells you what a bike is like from a picture and I always expect to work on my bikes some.

A picture won't necessarily tell you what condition a bike is in and price is just a number. Look them over and get the one you like best.

It's not different than any other mechanical thing, car, cassette deck...

Chances are the bikes won't be too different. 80s and 90s(which the lower most likely is) are about as heavy as older cruisers, they might even basically use the same parts, sans drum brake. Murray was always a cheap bike and both are good deals and the older one despite 40 maybe being too high, especially since female bike are far more abundant, some scrooge could be asking $100 dollars just because it's vintage, regardless of it being a dept store bike and a womans bike. It was probably $40 new.

Other than that it could come down to condition; are they botg ride-away bikes or need something(s) fixed first, or if one or both has a standard size front wheel axle or not. If it comes to replace a front wheel and it has that old standard inch dia axle- which cheap 80s and early bikes often come with as well; a modern(mid 90s- current) 1¼ axle won't fit that fork.
If they both could be easily repaird without a co-op or bike shop consulting their clan elder, who then refers to the ancient Sheldon Brown grimoir to set an excursion to the basement catacombs, then it comes down to fit and looks.

I like the top Monterey of the two... at least to my eyes, it seems to have bigger tires, less extreme sweep for the handlebars, and a smidge smaller chainring.

Tan one. Easy access. Fenders keep you and your basket and rack clean. Looks like the handlebar can be raised considerably higher for a leisure heads up style of riding.