Well one question is what sort of soil are you starting with? is it grassed? Do you have a tiller? 5 acres is a lot to start with, don't get lost and remember Baby steps.
What sort of sun exposure is there throughout the day? and water? are there hills or winter water build up/saturation issues, if so how can you turn them around into providing or being stored in biomass. (I find standing outside in the failing sun is the best time to see the typography in land)
Next is to think about your markets, and how intense farming production you want to get into. Salad and Tomatoes in my minds eye are best cash crop, specially in family/residential hustle zones.
Carrots, parsnips, potatoes, are the best Return Cash Crop, less labor if done properly too.
I don't know if you've rehearsed your zone's grow charts, but it's always important to focus your energy and day time (Because you will learn you only have so much time in a day) on your cash opportunity but it's also important to provide other varieties of crops and colors to keep customers interested!
I am doing the same thing as you pretty much but have all my factors in play already. for you I would truly consider the longterm preposals if farming is for you, because farming is not boyscout camp for the summer, you start, commit and continue. Do you plan on running these lands for numerous years? if so you should consider just putting 1/2-2/3 of all into instant covercrop, unless you have to do it by hand then you are just going to feed a lot of birds. I personally enjoy growing 2 biomass plants for every palatable plant. You NEED the biomass amendments and can use certain crops to feed your chickens! and RABBITS!
I recommend rabbits, they are a cuteness draw to selling veggies, they eat weeds and grass and a single bale of hay per rabbit for a winter, and if you grow food for your animals it will elevate the overall costs and boost PROFIT! both these animals can be enclosed entirely in mobile cages and dragged around for further food eleviation.
But for starting, you need to stand outside.
Look at your fields, consider the most efficient and effective approach to EVERYTHING.
and then start by figuring out how you are going to loosen the soil, where your paths will go so that you can reach your 2-3' arm in every direction and touch everything (meaning 5' wide beds)
I know permaculture talks about 'no till' but you have to start your loose soil by loosening it, then dig out paths around your beds and add that soil to the bed (making the bed raised enough [4-5"] dont raise beds TO high otherwise the peak will be dry, and all plants will grow around the base of the mound) also with good design, no one will even feel like they aught to step on the beds.
At night figure out your general crop rotations, water availability to each sector of your fields (design everything around water) and where the main paths are easiest to reach everything, and where the human walking paths can comfortably be with less bends as possible.
Then start thinking about your customers, What will they want, candy food? (radish, cherry tomato, salad, sweet corn, strawberries) or more bring home organic supporter family food (potatoes, onions, leeks, beans, brassicas, squash) or will you be serving a slave duty to restaurants (salad, cooking turnips, celery, bulk herbs, beats, potato, mass tomato, more salad)
Then start fitting your annuals into the blanks with proper rotation, and considerations for all the other elements of time & energy you want to contribute with your investment returns roughly sketched out. All along while you think about the long term which might want to be filled with fields of perennials like raspberries, strawberries, blueberries, blackberries, orchards, asparagus, horseradish, rhubarb, artichokes. if you decide a long term layout, how can you then plant them berries and also plant between them with your 2:1 biomass to food guild set up to help nurse the plants (not overcompete) and feed people.
Try to fit all of this into a budget while considering all of those unseen costs that are going to come when you need a piece to fix your whatits, or 10' of piping to finish the whosits, or seed tray materials, watercans, tools, rent.
I recommend learning to scavenge, it's your best survival skill, since you are with a church community it will be wise to connect your community to your actions through a blog or networking tool that you can broadcast material, financial, help needs and engage others, overall growing the organic movement in it's natural way.
That is my rant, accept it.
and consider building scrap material broad forks, buying greenhouses (can get 10x30' 6mil for $170ish w/ pvc ribs) write down everything you start and spend and pretend someone you admire is constantly reading it when you do. Get in shape, eat good but also fast your body, don't ware gloves unless it's sharp or shit, in 2 years yuor skin will be leather.