Resource for planning a new fruit orchard

Hello, my beloved fruit farmer has dropped the bomb- he’s not going to live forever and I better plant some trees if I want to continue to have my beloved plums and apples. I’m in a lack of fresh fruit induced panic and started trying to plan my little orchard. He’s going to order the trees for me for next year to save big bucks but I need a plan!
While he grows my most favorite varieties he’s an old school, commercial, spray a lot, straight rows kind of farmer and I’d rather create something more natural and I don’t want to mow anymore.
My best available site is our useless front yard giving me a space of up to 300’ wide and 35’ deep before the shadow of our decorative trees would start to infringe. One end of the strip (maybe 30’) is very wet in the spring and the other end is shaded in the afternoons.
For simplicity’s sake (and budget) I’ll have to have a long term plan that I can add to each year.
My ultimate goal is to feed my family and have enough to can for extended family and friends. I’m planning on 1 of each variety except my most critical (ginger gold apples for winter and Prune plums for canning) which I need to succession plant on different years to try and be sure I have one fruiting each year.
Between the plums, apples and possibly pears  with all their assorted pollinators I’m looking at eventually about 14- 18 trees (someday).
I know which main trees I want to focus on but after that my plan gets very hazy after that.

This is our front yard and needs to look what I think of as deliberate. It’s okay if it’s not ultra tidy but it can’t look weedy or insanely overgrown or my hubby will be totally stressed out.

Sorry this is so long, I suppose my ultimate question after all this rambling is “where do I start?”  
Free online resource recommendations? Books I might be able to get from the library?

PS- My farmer suggested I just start planting. Today. He’s braver than I am though.

I always start with a plan.  I might not follow it exactly but I think it saves effort.

I start with an aerial drawing or image.  Then I make a list of everything I think I aught to grow.  Then I put it together like a puzzle, trying to keep beauty in mind.  I then take stock of anything that didn't fit or openings on the landscape and adjust accordingly.  

When implementing the plan, it's best to start with earthworks, then trees, then the understory. If your going for complete sustainability, It might take a few years to fill in the whole ecosystem with this method, but plants grow in their own unique ways and this helps you take advantage of that.

I do all sorts of research online as to what grows in my zone.  I browse plant catalogs and circle my interests.  Most companies will send a free catalog. I keep some in stock to share with clients and friends who may want some inspiration. Every year I seem to discover a new variety or species of interest.

So,  that's my 2 cents from doing edible landscape design.  

Good luck!!

Since you have someone who knows what he's doing assisting you, it seems to me you need decide on what size trees to plant. It's my opinion that the smallest trees won't look good on your front lawn. They barely grow, there's a lot of holes in their mini canopy, Full or semi-full trees will require a lot of trimming or grow so high that you won't be able to harvest the fruit. So I'd suggest semi-full size trees that you keep trimmed with appearance as one of the prerequisites.

I'd also start off the first year planting the varieties that take the longest to produce fruit. Like pears, assuming you want pears. And then a lot of folks will suggest you plant the quickest to production in the beginning. I'd also keep track of what varieties of each fruit you prefer. Which variety of apples, or peaches, or pears. Write them down as you buy them this season. Know what you like, but let your friend/expert advise you.

You might also get a soil test so that you can start improving your soil this year. I don't know Michigan but usually a state college has an a soil extension service. On google it looks like you want to get a test kit from MSU. Check with a local nursery, they'll know. They'll also know what type of soil you have in your area, If it's clay, if it's acidic soil. Don't let me get you scared off. Most gardeners deal with adjusting the acidity of their soil. Once you know what soil you have you can plan on what you're doing and where. If for instance you have acidic soil then you can grow strawberries and Blueberries with out adjusting the acidity. If you have acidic soil and do want to grow those berries then plan where you'd want to grow them on your property so that you don't lime the soil where you want these berries. But then you don't want the lime washing into your berries so you need to do some planning.

My advice is to read up on the varieties you want, and then spend some time in the area you're going to plant just thinking. To be honest, when it comes to planting an orchard, mistakes just happen. You don't know what you don't know. The odds are high that however you plant you will look back and think that if you could do it again you would do it differently. Maybe you'll wish for two of a certain tree because you'll end up liking it so much, or this tree or that tree are susceptible to a disease or pest you don't like dealing with. However the odds are also good that you won't regret anything that much, because it really will turn out great almost no matter what. I share his opinion--start planting. No one is getting any younger. My advice is also to plan on a little redundancy, because trees do die. What I mean is to not go bare minimum on pollination or varieties you like. I like to plant in groups of at least three, with all three pollinating eachother. That way if one dies you haven't lost everything. A friend of mine planted two pears and one didn't make it several years in, so now she has to plant a new one. It'll be a few years before it catches up, and in the meantime she can't expect pears from the survivor because it doesn't have a pollinizer.

Good luck with the orchard. I hope you keep us in the loop for how it develops. I love watching them go!

If your fruit farmer would be a good person to ask some of the basic's as he is growing them for you now and he should be able to get you off on a general start to what works in your area and just because he grows conventionally does not mean he does not know other method's or can point you to some one in your area that does it differently. Also check in with your local agricultural  agent or local farmers coop, or farm supply store. just be sure to use a good nursery and not a flashy mail order catalogs that does not have good customer service on their products. Many different named ones have the same mailing address and have poor product and worse service. So have fun and enjoy as there is nothing like a fresh fruit off one of your own trees.  

When I was laying out a plan for what to plant where I'd consider the appearance of the trees, I already addressed the effect the size makes. You should also consider what the blossoms look like. Peaches are beautiful in bloom, so is an almond. There are a few red fleshed apples that also bloom a beautiful pink to red color. Some of these are Redfield, Pink Pearl, and Pink Pearmain.

The Redfield is available from Fedco Seeds, in Maine, and the last two are available from Greenmantle Nursery in California. The red fleshed apples aren't that great for fresh eating, but make an excellent sauce or an addition to pies and of course to cider. The Redfield was used as the only apple for a famous cider colored by the apples red flesh. While we're talking apples consider planting an apple as a storage apple. I just planted a Black Oxford for storage and am second guessing not planting the Keepsake also a storage apple.

As long as you're using your front lawn for an orchard you can also make an unusual and beautiful view as you drive past your property.

Thanks everyone! I’m still a bit overwhelmed and think I need to do some more research before my first round of trees arrive. What are your favorite books or websites for orchard planning?

I like wild but mildly planned.  My goal is to make things look like a lush forest with pathways.  I try to plant in offset islands.

If you want a traditional looking orchard and you don't want to spray check out Stefan Sobkowiak and his trio system.