I've got about an extra thousand dollars in my bank account
a couple of kegs and CO2 tank and a regulator are not really worth a thousand dollars, but I agree with you - kegging is definitely more expensive than bottling (if you don't take into account your time, which is money). If you asked me 2 years ago, I would have said bottling is great. Don't fix what's not broken. I actually enjoy bottling and I still do it sometimes. Very relaxing (albeit time consuming).
But while almost everyone who is kegging has started with bottling, virtually nobody I ever heard of who went to kegging has sold their equipment and went back to bottling. I know more people who went from all-grain back to extract or people who went from 5G batches to 1G batches, and I mean it.
There are many reasons for that. Yes, a 5G keg at $30-50 or so is a big one-time cost for many, but it saves hours in labor (not just bottling but also cleaning and storing bottles) for every single batch, every single time. If you brew once a year, stick to bottling, but if you enjoy brewing and want to scale up to brewing more often, it's a great investment.
If you ever want to brew a great IPA, kegging is the only way to go, no way you can get even close with bottle-conditioning.
Separating sediment from the beer, force-carbonating with CO2 (over just a few days) and being able to dial it up or down, conditioning the beer while being able to drink/taste it (and fill bottles as needed) is ideal.
You can make secondary additions of various ingredients to entire keg (hopping, wood, lactose, coffee, cocoa nibs, peppers, fruit, etc.), in other words keep experimenting with the beer, while drinking it.
You can do beers on nitro, mix beers from different kegs, pour as much or as little as you like, fill growlers or bottles, etc.
I enjoyed my bottling days, they were great, but there is no way I abandon my kegs now. Not even if you paid me twice what I paid for them.