It's probably not necessary to go nuts on gear spending, at least until you're absolutely sure you need to do so.
A bike stand is super handy, but it's not absolutely essential. It's one thing if you frequently assemble/wrench on bikes; during a one-year stretch where I was holding onto a friend's stand, I assembled eight bikes from stems and components, while it's hard to assemble more than one a year without the stand. But it's not impossible to do these things standless. The last three I've done happened without a stand, just on the dining room floor - even the work on brakes and drivetrain, where the stand really helps. If the more serious work is irregular/infrequent, you can probably get by without a stand. If you have access to a community bike shop, the stand/s they'll have will probably be adequate for the few situations that occur.
it's easy to go nuts with tool accumulation (guilty!), but the range of indispensable tools is fairly narrow. My own preference is to always have the tools to install/remove any crankset and freewheel/cassette I use, and not to use any crankset/freewheel/cassette I cannot remove. My neighbor Bill Lindsay can confirm this; I had a nice Phil Wood-hubbed wheel with a nicey-nice White Industries BMX freewheel on it that sat untouched for over a decade, until I was able to borrow Bill's freewheel remover and get the freewheel off this week. Other tools that are likely to see regular use are Allen wrenches, hex sockets and screwdrivers required to install/adjust/remove pedals and brakes/brake levers; the Y-style 8/9/10mm hex socket wrench and 4/5/6mm Allen wrench are often adequate for this, plus an 8mm Allen wrench and/or 15mm pedal spanner to install/remove pedals.
Since you're usisng a Rivendell, you're probably using a traditional square-tapered crankset. If you're getting deeper into drivetrains on these, a chainbreaker, a crankbolt spanner and the appropriate crank extractor for your crankarms are useful. Some more elaborate multitools have chainbreakers built in; I made do with the chainbreaker built into my cheap, no-name Taiwanese multitool for years before getting a nicer Park one. If your crankarms have self-extracting crankbolts, then the arms will likely pull off the bottm bracket spindle with an 8mm (usual) or 6mm (older Shimano Dura Ace/600) Allen wrench. If not, then you'll need the Allen or hex wrench necessary to get your crankbolts off (usually either 8mm Allen or 14/15/16mm hex) and then the extractor for your crankset.
Japanese, Campagnolo and all modern-ish cranksets use a 22mm extractor, which are practically the only ones made these days. But if you're using older cranksets (pre-80s, basically) from the French manufacturers Stronglight or Specialites T.A., the crank extractor holes may be larger than 22mm; older TAs are 23mm, and older Stronglights are 23.35mm. Don't use a 22mm extractor on an old French crankset unless you're absolutely sure it's the right size; it's easy to loosely thread the steel extractor into the aluminum crankarm, and then strip the extractor threads out of the crankarm when the extractor tries to pull the arm off the bottom bracket spindle. I'm not saying "don't use old French cranksets'; I use practically nothing but. But understand what you're getting yourself into first, and get your tools in order before you start. The French-sized extractors are available from a variety of sources (eBay/Craigslist/closing oldie bike shops for used,
Stein Tools/eBay for new), should you need them.
There's a lot of religious theories on grease. I like Phil Wood's green grease, in part out of reactionary sentimentality; I'm not sure that it works any better or any worse than any other grease, but it sure costs more. My compromise has been to use Phil grease in any situation where ball bearings are involved (bottom brackets, headsets, hubs, some old derailleur pulleys), and to use the muchcheaper Park blue grease in all other situations (frame/headset/bolt/axle/QR threads, seatposts, stems). There are lithium greases intended for mechanical assembly that come even cheaper in cans, that are reputed to be just as good (if not better). If I had that much, I'd almost certainly misplace the half-used cans and go ballistic when I couldn't find it. As it is, I probably have six half-used tubes of Phil and Park grease around, because I buy another tube whenever I can't find the one I'm looking for.
Speaking of which: Has the formula of Park's grease changed in the last few years? The most recent tube I got seems thicker, denser somehow; it's a lot harder to squeeze out of the tube than it was in previous years.
Peter Adler
Berkeley, CA