How much do you know about growing fruit trees? If you know little, I would suggest you star small, either a few trees or fewer vavrieties.

You do not want to be overwhelmed. Apple and pear are easier to grow than peach and plum.

Check out Cummins nursery and Adam County Nursery. They are two of many good online nurseries. They happen to have more varieties and good descriptions for you to start with.

I agree with the above. I started with 4 and was so excited I added 14 the next year (this spring). I bit off more than I could chew with regards to planting and ended up straining a back muscle trying to get everything in the ground quickly. If I might suggest, look at the dave Wilson fruit tube videos on youtube concerning backyard orchard culture. It's a great start.

Dave Wilson is a great nursery but it is based in CA, a perfect state to grow lots of fruit tree varieties.

You should also tell us where you live. Pest and disease pressure varies depending on location (even with the same zone).

I have had fruit trees on every property i have ever lived on. Taking care of them is not an issue. I was just looking for suggestions as to what trees i should start at my new property.

Peach trees are going to struggle in 5a. Red Haven may be worth trying. Contender and Reliance are hardy, but not that great. Contender is better than Reliance. I know nothing about apples and pears.
For cherries I would look at the Romance series for tart cherries.
For sweets some new canker resistant trees developed out of NY look good to me.
Adams County Nursery has them. You have to order very early, they sell out quickly.
Black York, Blackpearl, ebonypearl, and burgandypearl

I have White Gold which was developed out of NY too. Nice tree also!

And I have Carmine Jewel from the Romance series. Grows like a weed!

For now (2nd leaf), it is in a pot. These are high brix bush cherries, they grow about 6 feet tall and wide.

Here's a photo of the fruit from various trees in the Romance series

One of the most interesting trees I have is Nadia a sweet cherry-Japanese plum hybrid

http://i128.photobucket.com/albums/p181/whitenoise_photo/untitled.png

The easier way is checking Adam County Nursery web page. Look at its ordering fruit tree page. It lists apples in ripening succession. You want to spread your harvesting season of any fruit tree you grow. There are so many Good apples, some old, some new varieties. You should also check its Disease Resistant fruit tree list. Growing disease resistant varieties can be helpful esp. Fire blight resistant.

Another good place to check are orangepippin and Cummins Nursery.

Pear is also another easy fruit to grow. I like the Harrow series. They are good esp Harrow sweet which is self fertile. Avoid fire blight susceptible varieties. Do you want Asian pears at all? Easy to grow, too.

Peaches and cherry are more work. Peach is iffy in zone 5. Cold hardiness varieties are needed. Sometimes, is survives the winter but fruit buds get killed by late frost. Varieties that often mentioned are Contender, Reliance, Madison, PF 24 C or even Red Haven.

Cherry , Sour cherry has less issue than sweet. Sour cherry are self fruitful.. Evan/Bali are known for cold hardiness. Other choices are Montmerency, noth star, Danube, Black Tartarian.

Not Really sure how cold hardy is sweet cherry. The popular ones are Black Gold, whie Gold, Van, lapins, Stella. You can check out the Pearl series and the Romance series, the latter are bush cherry.