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Would you go all-grain or start legging first?

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If you don't have control over consistent fermentation temperature control personally I would start there!

If that's already under control then it does really depend. AG brewing introduces a lot of variables in process that you may not be ready to tackle. Kegging is an investment but pretty straightforward and easy to figure out.

Agreed 100%. Having the ability to precisely control ferment temps rates above getting set up to do AG batches. In a warmer climate or one with big temp variations, a used freezer/fridge with an STC-1000 controller is hard to beat.
 
When I first started brewing, I went, in order: extract partial boils, extract full boils, all grain, starters, kegging, O2. Then after having to sell off most of my equipment, then restarting, I went: extract full boils, starters, precise temp control, all grain, yeast slanting. I plan to get an oxygen tank eventually, but most of my beers are moderate gravity and have fully attenuated without the use of O2. The biggest difference in my quality from the first time to the second time was PRECISE temp control (like BigFloyd said, fridge/freezer with STC-1000). Kegging never improved the quality of my beer, not even with being able to control CO2 volumes, and since I actually enjoy the bottling process, making labels and giving away beer, I won't likely go back to kegging
 
Don't get put off all grain due to all the comments about fermentation temperature control !
Review where you will be fermenting and what temperatures are available to you, for instance on the floor is cooler than a counter top, a cupboard is warmer than the counter top, basement or upstairs, the time of year and weather, all these give you a choice of your fermenting temperature, that's before you get inventive with swamp coolers and the like.
Then it's yeast selection and what temps it wants, for instance the following are yeast that I use.
M27 Wants 26-32C
M07. Wants 16-22C
M79. Wants 18-23C
US-05. Wants 12-25C
US-04. Wants 15-20C
And that's just a few, design your brews around your kit, your recipe and your environments , we all have loads of environments to choose from !
 
I did kegging first. I still do extract brews and now planning to go all grain soon. For me, I just couldn't stand bottling. That's why I started kegging.
 
I did a few Extract/PM batches, learning along the way, and finding out AG was much cheaper. My BK is heavy SS, so i didn't really need a cooler/tun to mash at the correct temperature. I made a Zapap tun to lauter/sparge and was getting better results than before (I already owned a thermometer). I then bought a hydrometer to see if I hit the correct O.G.'s or not. My fermentation chamber was my crawl space in my old house (rental), and one we now own doesn't give me direct access to the crawl space (plumbing is in the way). I already owned a propane burner that came out of my old smoker, so I had heat again (no access to the stove as the b/i micro was too tall). I bought a 40 qt pot, so I could sparge and not have to use every available burner in the house to boil down my wort. Then, before I got to break in my new 40 qt pot, I landed a new 30 qt turkey fryer set up for $20.00. then came Christmas, so I am sitting on a new burner/pot setup until after New Years sometime.
Once, again, sorry for the long post. I still bottle, still use my Zapap tun, and somewhere in the middle of summer, I had an empty 5 cu ft freezer, so I built a STC-1000 controller, and I now have both heating and cooling if needed. I still have a system on the cheap as some of the things I needed I already had. I have what I need to brew 5 gallon batches of 1.050 beer, and will have to figure something out if I start making bigger beers.
 
I don't want to discourage you in an way from advancing into AG and/or kegging. I do AG (started with a mash tun and later built a 240V recirculating E-BIAB rig) and keg as well. It's really a matter of prioritizing the improvements/investments that will give you the greatest benefit to your brewing.

If I were forced to give up my brew gear man-toys (no offense Yooper :D) one at a time, the last thing to go would be my fermenter fridge.
 
I've been AG brewering for over 2 years and 40 batches. I still bottle. Kegging is more problematic than just the initial investment. For one, if I have a chilled keg sitting in the basement I would be much more likely to drink too much beer any time I walk by the keg I'd top off my glass! The other big benefit of bottling is ability to easily transport your beer to different places or give away beer as gifts. I also often have 4-5 different beers in bottles. If I kegged only I'd only have a couple choices.

On the other hand, it's not that hard to bottle from a keg, although I do see your point about drinking too much from a keg, but that's a different problem altogether and may be just a personal issue.
 

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