Do you normally get much fruit? I've thought about planting some fruit trees but from what i've read it is a lot of work to keep them undiseased and keep the pests away, insects and animals. I don't have a large yard so I couldn't plant anything close to as many as you even lost.
Pick the correct tree for your lot in the world, give it some minor care, and you will likely do well. For example, if you plant a pair of basic pear trees in CT (pretty much anywhere), you would be hard pressed not to have a load of pears in 3-5 years. They will not be the pesticide-treated ones you see in the store, but they will taste as good or better, and if you can deal with a few skin blemishes, it will be some of the best fruit you eat. My MIL had a bartlet pear in W. Hartford that gave her enough pears to jar up about 20 or 30 quarts every year with plenty of fruit left over. In general, pear and apple are very easy to grow and produce heavily without much work. You can make apple juice and apple sauce very easily. If you want fewer misshapen fruits, you can dose them, but I never do - I don't mind eating the skin of an apple with the unappealing patches of whatever on them that don't affect the flavor at all - just more random DNA for my gut to cut. Peaches are trickier, but peaches off a tree are the best peaches you will ever have. I used to love mowing around the trees a just picking a peach as I went, eat it, juice running down my face, sweet as can be. But, as I noted, peaches are not cold hardy, and I lost a bunch this year. Prior to this, we have had several bizarre winters/springs, so my yields were low. One year it got to 70 in mid March for a week, everything bloomed early, and then was frost killed. One spring it was wetter than wet and very little pollination occurred. The other year summer was bone dry and we got very small fruit. Apples and pears did reasonably well in most of those years. Apples tend to produce heavy then light or none, then repeat. Pears (particularly Asian pears) tend to produce great every year for us.
In sum, for 25 bucks you get a pear or apple tree. Plant 2 if no pollinators are nearby. Plant it, water it once a week during June/July/August, 1/2 that in May and September, 5 gallons if you don't get 1" of rain that week. Do that for 2 years. Keep the weeds down out 2' from the branches - a quick spray of roundup (glyphosate) is best. Light mulch is next best. Plastic or thick mulch is bad. Sawdust will kill your tree if used as mulch. 3 to 4 years after planting you may see fruit. 5 or 6 years later you will see fruit.
Look around, ask neighbors, and so on. Apricots don't do well in CT. Plums will, if the right type. In any case, plant something you like. I planted a bunch of gala and later wondered why I did - I don't really like gala.
