The length of your season may be the limit of production on a indeterminate tomato. Long seasons, more fruit.

WRT taste, and ripening off the vine, I've found a huge difference between ripening in a 'cool room' where the temperature ranges from 65 to 70F, vs ripening upstairs in temperatures that tended to 75F and above.
Ripening in 75F and above, I found that tomatoes tended to converge on a single taste: "tomato" "it's a tomato" "it's a soft, over-ripe tomato".
Off the vine, a lower ripening at cooler but not cold temperatures (not below 60F) produced the best textures and tastes from all tomatoes I've grown.

Taste testing when growing out crosses is the final judgement. Like karstopography said, no distractions on the palate. I take a slice from top to bottom for tasting. I will lay out a few to compare. I give every bite some time for aftertaste, because that is important to me, personally. What is the taste that lingers after you eat it.
So I get my first impressions, it's a tomato... it's a sweet tomato... it's a tangy, tomato... OMG it's as good as an apricot.
And then I do repeats on another day, and get other folks to taste. Rarely changed my first impression, though, on any tomato.
But it is true that the really good ones, you get even more nuances the more individual fruits you taste.

It depends on how much you're willing to put into it.

As far as the easy varieties to get to produce a lot, for me, those are these:
- Brandywine Pink (my strain of it, if not the variety at large, too; it appreciates fertilizer and black plastic to warm the soil; I prefertilize the soil a while before the plant is there)
- Galapagos Island

Here are some others you might consider for production:
- Mountain Princess
- Pakenham Pear
- Aunt Ginny's Purple (more difficult than Brandywine Pink, but if the conditions are right, it produces plenty)
- Orange Jazz
- Sausage
- plenty of others

Really, though, I think the soil matters more than the variety, for many varieties. A great variety can totally underperform in the wrong soil for its needs. I say this because it seems like no matter what I plant in the best spot in the garden always produces a lot! And most things I plant in some parts of the garden don't do much.