We've been buying a side of beef each year for many years. Good points already made. These would be my questions for a person from whom I'm purchasing freezer beef for the first time...
First of all I want to mention that where I live, the purchase of the beef is an actual purchase of the animal and the processing of it is separate. What that means is that I pay the farmer an "on the hoof" price, and they are responsible for taking the animal to be butchered. Then I pay the processing plant a separate bill for processing and packaging. So this is the perspective I am coming from for this and is only from my personal experience. Others may have a different experience and things may work differently where they live. So, as a guideline...
1. What breed is the animal and what will be the grade of beef? Choice? Prime? This will help you know if you are getting a good price. The grade determines the yield you will get. That is, the higher the grade of beef, the better yield (and therefore a better deal). Ask the age of the animal.
2. Do they base the costs off of the market price the day the animal goes for butchering or do they have a set price per pound? (That price will be "on the hoof", I've never heard of anyone doing it any other way.) They may have established a price of, say, $1.25/lb. on the hoof or they may say that they will charge 20 cents per pound (again on the hoof) over whatever the market price was that day. Definitely understand the pricing, as this will be the bulk of your cost.
3. Unless it's organic, it most assuredly will be grain-finished. This is to put WEIGHT on the animal before butchering. Ask what they anticipate the weight to be before and after finishing. If they are butchering at 900lbs. you are not going to get as good of a deal as you will if it is closer to 1200lbs. 1100lbs. is a good weight.
4. The time of year they butcher is also key. If it's in the Autumn, which (IMO) is the best time to butcher, then they have probably been eating mostly grass all summer. I personally LIKE the flavor, but it *is* different than supermarket beef. If it's in the Spring, they have been grain and hay fed over the winter and will taste less "gamey" than those butchered in the fall, but may have more fat (which isn't bad... this goes back to question #1 about the grade of beef).
5. Ask about medicines used, of course.
Many of the rest of the questions will be ones you want to ask the processor, not the farmer. The farmer won't know about this stuff except how they order their own beef. Definitely get in touch with the butcher to find out the following:
6. If not purchasing a side (if purchasing a quarter, for example), how are the cuts of meat divided? For example, if you take the hindquarter, what do you get vs. if you take a forequarter. Do they equally divide all the cuts of the whole side or do you get just the cuts from your quarter?
7. Of course you'll want to find out the processing costs. These are almost always based on hanging weight at the time of butchering. The processing fee is how much they charge per pound to process your meat and it is based on standard cuts. Around here, it's about 40 cents per pound hanging weight (which is after the feet, head, hide and entrails are removed, but is still on the bone.) If you want specialty cuts (for example Porterhouse, rib roasts or if you want to keep the filet whole), they may charge extra. Research the cuts beforehand so you'll know what to ask for. Also when asking about how long they age the beef, ask if they dry age or wet age it. When they dry age, the total weight when packaged is reduced, but the beef is usually more tasty. Most places age for 14 days. If it's longer ask if you pay extra. There will be a butcher cost on top of processing fee... find out what it is.
8. Ask about how the meat is packaged. You can usually specify things like 2 steaks per package or 4 steaks per package. 1lb. of hamburger per package or 2lbs. per package. How large you want your roasts cut. They may charge you extra for smaller packaging and if you want your roasts or steaks deboned. They will also want to know how thick you want your steaks to be cut.
9. They will probably ask if you want certain cuts to be put into the hamburger (Arm roasts, for example)... I would do this if you use a lot of ground beef and prefer leaner beef. I changed things up this past year and didn't get the extra ground beef and regretted it.
10. Ask how long they will keep the beef frozen and what the cost is for that. Sometimes if you don't pick it up within a few days they charge freezer rental. This happened to me once when the person I buy beef from took the animals to a processor that was almost 2 hours away and I couldn't get down there for a week or so. During butchering season, they schedule when the animals go to slaughter and sometimes butchers are booked up for months, which is what happened to my supplier that year.
11. I'd also ask about getting some suet in addition to bones and specialty parts.
12. Finally, I'd downright ask for a sample from last year. Tell them that you want to try a pound of their ground beef from an animal butchered last year to see if you like it.