Need advice on image resizing methods

Here is the site I’m working on. I have 3 sizes of thumbnails on my homepage with different behaviours. Not being a strong WordPress developer (yet), I looked to plugins that would solve a few functionality issues which helped but has left me in a slight state of confusion.

1 – 129×129
This is generally working the way I wanted so no real issues here. I used random-image-block which I had to modify (to strip out a few unnecessary divs etc). Since it’s a widget plugin, I’ve had to pull in the sidebar at this location. It doesn’t feel like a neat way to do it but it works. If it was maybe written on the page instead, I could maybe figure out the other issues easier…

• displaying random thumbnails in a 3×3 grid
• links to the images project page

2 – 389×387
This kinda works although all it’s doing is displaying a random image from the uploads folder and stretching it to the correct dimensions. Another plugin has been used. This time random-image-selector…

• Main image that should display a random cropped (not stretched) image
• Nice to have would be a rotating gallery of images?
• Doesn’t have a link to the images project page currently but would like this added like the 129px

3 – 185×140
These are the loop which displays the latest 4 projects. I set a featured image and it displays a ‘medium’ version. This works mainly as I want but I’m cheating by hiding the overflow on the div. The images are not the correct size so it’s only display the top half. I would like this redone so that it takes a better cropped image…

So there are a few issues there. Looking for suggestions to maybe simplify. I think the worst problem I have is number 2. The stretching looks awful! It’s currently selecting a random image from the upload folder which has thumbnails and all in there. Is there possibly a way to organise my Media Library into folders ‘thumbnail’ ‘medium’ ‘large’? Then I could just target the correct folder in the plugin settings.

I tried to be clear, not sure how successful I was though. Hope it makes sense. Thanks to everyone here at this community. I’ve learnt a lot but still have a lot of learning to do.