I think a lot of our choices in equipment say more about who we are than about brewing.
I have resisted kegging for quite a while, but I now switched sides and think kegging is not just for convenience/time saving, it does produce a superior tasting beer in many regards.
However, I also believe that without going full kegging route, you can produce excellent, even outstanding beers with just $300-$500. I still think that if you don't mind bottling (and have plenty of time) and money is an issue, bottling is the best way to have the best variety of beers and solid pipeline for very little equipment investment cost.
Kegging with proper serving equipment (keggerator/keezer etc.) and all accessories will cost you a few grand (in my opinion once you go kegging route, it is silly to limit yourself to 1-2 beer options, might as well go for 4-10 serving options!).
Currently, more than 75% of my equipment purchases are related to kegging and serving from kegs (taps, kegs, regulators, tanks, connectors etc.).
But kegging also allows me to scale up easily and brew more, without the overhead of time/effort spent bottling, which makes me a better brewer in the end, so it's somewhat justified for me - maybe for you too.
What I still don't quite understand is the appeal of much more fancy equipment - like automated brewing, stainless fermentors etc. If money is no object, sure, of course, count me in - but the benefit to me seems mostly cosmetic or very modest time savings, while expenses sky rocket, while quality of the beer should be about the same.
The approach a lot of us undertake: $50 DIY 60qt. plastic mashtun and $100, 20 Gallon Aluminum pot, a burner and immersion chiller (DYI in my case), maybe DYI stirplate, combined with 10 or so fermenters, some glass, some plastic, and a lot of kegs, is the cheapest route to establishing a pipeline that allows brewing weekly or monthly 10-15 Gallon batches, splitting them up for various experimental hop or fruit addition, with fermentation temperature control, cold-crashing, ability to serve numerous batches, have room in pipeline for 1-year old sour aging or 3-month+ strong beers, etc. - for a relatively modest investment of maybe $3K or so.
To me this is the most versatile, flexible and inexpensive setup that while perhaps not the most elegant or visually appealing, does accomplish the task and does not compromise quality whatsoever - and can be adopted to almost any home-brewing schedule requirements, up to 30-50G per month.
The alternative is to have a much more fancy setup that cost about the same, say $3K, or more, but limits you to a single 5G batch at a time and also limits you to 5-10G per month, no long-term aging beers (like sours or imperial stouts) and serving 1 beer at a time.
