I'm probably going to buy a 1/4 side of beef for the first time this year

Any absolute red flags?

There are 2 producers in the next town. One wants a $500 deposit, the other $300. The first's retail price/pound is > than or equal to my coop's price. The 2nd is just under $8/lb. So, my inclination based on price is to go with the 2nd guy.

But I"ve never bought beef in bulk. What should I look for in terms of cuts? Package size? Quantity in the 1/4 share, etc?

Any info would be appreciated!

I purchased a 1/4 cow and really enjoyed my process. The farmer took me through the whole process and guided me through as I was not used to a cut sheet and what to expect.

I have seen a few different ways that a quarter is sold. Mine was a split side so I got a little bit of everything. I found out that I could get a bit more bones/offal if I wanted them due to others purchasing not wanting them. A quarter beef where I am is somewhere in the ballpark of 100 pounds plus or minus twenty pounds... ish. Just know that if you are truly getting a quarter beef from one cow, if you want chuck roasts  and other fattier cuts your grind might be a bit leaner than you are used to.

Something I did not pay attention to very hard was the breed of cow and how they are fed. Some folks care if they are grass or grain fed and how they are 'finished'. The type of beef I purchase comes from Blonde d'Aquitaine and they are a leaner type beef.

I've only done this once, so I don't have any good advice on who to pick or what to look for.

However, I want to remind you and any future readers that even 1/4 cow is quite a bit of meat. You want to make sure you have room in your freezer BEFORE you buy :)

We have bought a "rancher" PAC for the last few years.
Apx $450 for #70 of meat, but we cannot choose what is included.
Ranchers Special – Just Over 1/8 BEEF
4 PK Rib Steak (1/PK)
3 PK T-Bone Steak (1/PK)
1 PK Porterhouse Steak (1/PK)
2 PK Top Sirloin Steak (2/PK)
3 PK Round Steak (1/PK)
3 PK Chuck or Arm Roasts (3-4 LBS ea)
1 PK Rump or Sirloin Roast (3-4 LBS ea)
2 PK Short-Ribs
1 PK Soup Bones (Neck)
25 LBS Ground Beef
TOTAL – 70 LBS

I second making sure you have adequate freezer space.

From what I can tell, I need about 5 cubic feet of space for the freezer space. I have an available stand alone freezer. Of course, right now it doesn't have 5 cubic feet available. One of my jobs today is to figure with my partner's help how many shelves that would be or if it would push out all the other food I store?

My reference is here:
https://simpsonsmeats.com/blogs/blog/how-much-freezer-space-for-a-half-cow#:~:text=How%20much%20Freezer%20Space%20for%20a%20Quarter%20Cow%3F,less%20than%20half%20the%20price.

And I rounded UP, not down from what I found...

Years ago, I purchased packages of meat sold as 1/4 cow or 1/2 cow, etc. similar to what Thomas mentioned.

The meat is only as good as where the beef came from so my suggestion would be to use a reputable meat processing plant.

I am with Anne on this …reputation is the most important factor.

Agreed!
I have used this same N. Idaho butcher for 40 years, a family business.
They raise their cattle to butcher; they grow the GMO-free grain they are fed.
This is where I bring the piggies each fall to be turned into little white frozen packages.

This falls under the heading of "Know your Farmer".

We buy 1/2 cow, every other year (the alternating years, we do a whole hog). The cuts you would likely want are the same as you'd buy through the course of your normal consumption - if you have the choice. We've purchased from local family farms and from big farms, a couple hours drive away. I'd strongly recommend, as Thomas did, getting to know your farmer, how they raise & slaughter their animals; feed, philosophy (of that's important to you), check out the farm. Is it clean? Do the animals seem happy & healthy?

We've had a couple we will never buy from, again, either because the cuts looked like they had a toddler in charge of the knife, or because the meat was off, we think they'd cut through the spinal cord, and tainted the meat), but most of our decisions have come down to what we learned, from my first paragraph, price, convenience, and whether we get to choose our cuts. We prefer whole muscles, and about 100# of ground. If we didn't get a deer, then we want even more ground, because I make the raw food for 2 of our 3 dogs. Otherwise, we'd likely only go through about 50#. Like Timothy, we also get the offal & bones. We like the tongue, heart, & liver, as well as bone (broth) & marrow. So do the dogs!

My one last bit of advice is that if you're not entirely satisfied, don't give up, because it seems like every farmer/slaughterhouse combination is different, with different options, different costs, etc. Good luck! Our last 2 cow halves & pigs averaged about $3.50/#. Can't touch that, in the store.

We got 1/4 of a cow this year from a local family.   It was a little more than I could fit in the freezer section of our standard fridge.  We got all the different cuts.  
It has been so nice to have plenty of steak and hamburger.
Next year I will ask for some fat and bones too.  

I like the family we got the meat from and I visited with them about how they manage the pasture and keep the cows healthy.  

Raising cows is too much work for me and I am happy to support our friends.  

After a lot of discussion, my husband pointed out that we hardly eat beef now. Which is true. Years ago, when ground beef got to be $4+ a pound, I stopped buying hunks of meat and only bought sale meat or ground. I got what I'd swear was "pink slime" from our local market and have never bought meat they process there since... At the time, they were nearly the only game in town, another factor in our beef reduction.

So, recently? We use about 1-2# of ground beef a month and maybe 8 other pieces of beef (steak, kabobs, roasts, etc.) yearly.

My revised plan is to get to the local beef producers and buy some ground beef from them for a trial. Seems like a better idea than spending $100s for something we haven't been eating lately. Or, I can just put up and shut up about the coop's pricing and buy from them, which is what I've done for the past 10 (?) years. Also, there's another coop I belong to... my perception is that their prices in general are much higher than the one we've belonged to for decades... few if any bargains anywhere. I've never bought meat from them accordingly.

The "old" coop is in an artsy-fartsy/hippy town, the "new" one in a state capital....

It helps to ask lots of questions. Think about how you would like animals raised, any foods or medications you would not want them to have, and ask about those things. Some farms will be open to you inspecting the farm and might have regular farm open days, or farm pickup. Good things to see are portable electric fencing, weeds, cows looking healthy and happily grazing.

Abattoirs can sometimes be dodgy and and can misplace one farm’s meat and replace it with someone else’s, and other stuff that we don’t want, so the combination of a good farm with a good abattoir (preferably on-farm slaughter) can be important.

An important thing to consider is whether you are getting the front 1/4, the back 1/4, or a split half. Personally, I like a split half, because you get a bit of every cut.

Have a think about what kinds of cuts of beef you like to eat, or what you would eat if price was no issue. We eat a lot of ground beef, and just the usual offcut ground beef alone isn’t enough, so I usually will get the chuck as ground beef too and that is enough.

There's diagrams around online about the different parts of beef, and which cuts are an option for each part, so it's good to be familiar with this, as well as being familiar with your cooking habits.

If you want bones for broth, fat for rendering, and offal, make sure to request those before slaughter as they are sometimes thrown away as "waste" if people don't ask for them specifically.