Can you post a picture of the plant?

Often ill plants hurry up on ripening their fruits. Also damaged fruits ripen up faster and fall off. We have seen this in apples and other fruits with worms. I would cut those tomatoes and check if there is a worm hole or other insect damage on them.

All the plants appear healthy...

Usually green shoulders and uneven ripening as shown in your pic is caused by excessive heat but you say it has been cooler than normal.

Then the next most common cause of those symptoms is excessive sun exposure on the fruit yet your plants look like the fruit is fairly well shaded by foliage, at least those in the photo. So when you bring them in are you placing them where they can be hit by the direct sun on the kitchen counter? That would explain it so make sure they are kept out of the sun.

As to the fruit drop - quick release - that too can be weather related and is also triggered by excess nitrogen as well as several other plant stressors. It isn't actual fruit abortion but the cause is similar - plant stress so it sheds the fruit.

That stress could be just the "lot of rain" effect on the roots and cooler temps - which you can't control of course. Just make sure there aren't any stressors that you can control and then hope for an improvement in the weather.

I think all of us who had a bad year last year due to drought held out high hopes for this year thanks to the early wet spring. Unfortunately because of the ongoing wet weather and cooler temps few of our hopes are coming true. Little comfort I know but it's the nature of gardening some years.

Dave

Dave,
As always, thank you for your help! I'm just so frustrated after having such wonderful success last year with this variety (10 quarts/38 pints and many, many eaten fresh). This year, they aren't shaped the same (more pear-shaped than the oblong ones we had last year). It is different seed, but same seed source and variety.

I'll update this post as the season continues.

Here's hoping there will be a change in the weather and we all have a better harvest than we thought!

Cheers!

Some very nice pictures there, I am growing some Roma too and those pics may give me some help as to when they are ripening, they seem to go from a lighter to a darker green first.

Cannot really off any advice on the toms though, at least not expert advice.

All I can suggest, on the positive side is the that the plant knows best and decided to drop those fruits, perhaps because it had such a big crop? Too may mouths (tomatoes) to feed? But why would it drop them? Well maybe if they rotted on the plant the whole plant might become diseased?
Sacrificed for the greater good?
I am just guessing of course, I am a novice grower, just trying to apply some tomato logic.
I guess it remains to be seen how the plant will get on.
There is picture of my Roma in the linked blossom end rot thread. I am just wondering how long that big one has tell it ripens. I think some of mine fell off last year too, but they were all hit by disease. I would consider ripening ones falling off a success, none of mine got that far before disease set in!!
I'm in the UK though and they are outside, so I was never expecting much, I started earlier this year and am hoping things will be better this year as the weather has been better (sunnier) too. All my plants are twice the size as well, it's like a jungle out there!!!

Best of luck with the rest of them!!

Here is a link that might be useful: my pic in blossom end rot thread

I am having the exact same thing happen to my paste tomatoes. Other tomato varieties are not falling off. I am thinking the rainy weather, and the very cold nights which began in early August here in NH. I, also, am growing under the same conditions (type of beds, compost, etc as the prior year, when I had a terrific harvest with hot sunny days).