A Gardeners Forum Forums General Discussion Plant pests and problems Pests in my tomatoes and pears

Hello. I'm new to the gardening world. Bought a house and last year was my first attempt at anything. Located in Queens, NYC. It's around 50-55 degrees during the day now and 40 at night.
My house came with an old pear tree. We got lots of pairs last year but the majority of them had a type of brown rot on the bottom of the fruit. The rot area got bigger and softer, the longer we left the pears on the tree. I never saw any bugs. The tree is just starting to get buds now.
I planted tomatoes and got tons of them. It seemed that in only 1 or 2 plants out of 10, I had some tomatoes with a perfectly round hole bored into the fruit. In one I found a type of slug or worm, pretty small. When should I plant tomatoes this year? Last year I started real late, around July.
Thanks, -Rocket

Here in Texas we've started our tomatoes already. Daytime temps 70-80, night time 50-60. I like planting marygolds around my tomatoes. They're a great companion plant both for the worms and insects as well as for the soil.
As for the pears, are they being left on the tree too long? (I don't know a whole lot about friut trees)