Apart from book reviews and exhibition reviews, very little of my blog would be text only based. Most of the exercises, research posts are text plus an image or two. Therefor I have have found little problem with uploading images.
I use primarily 2 photography software packages. Lightroom for storage, and general exposure work, then Photoshop Elements for greater toying with the image. Once I complete the work in Elements, it goes back in to Lightroom for storage, gets backed up on various storage devices, and held as a psd file. On my handy storage device (a Lacie USB key ring) I have each image stored in its particular exercise. These are then generally grouped together into Chapters for storage on other back-up devices.
I also make a jpg file, which is uploaded to WordPress. Each image is uploaded into the main group – and not really segmented very much on WordPress. Generally I upload more than one image at a time – and just leave them ticking away while I work on something else.
How I show the image on WordPress – on the actual blog post – depends very much on the exercise, and then number of images. It is not unusual for me to have a single image shown, nor a grid format. It depends very much on the post itself.