I have never had this come up and I can't find anything saying you can't, but can you attach 2 Technical Machines to the same Pokémon at the same time?
There are no restrictions on TM's that say you cannot, so yes you can.
Source: PUI Rules Team (2006-01-26)
Could I play a trainer if it's obvious that it will have no effect (i.e. Life Herb on a Pokémon without any damage and with no Special Conditions on it)?
No, you cannot play a card if it is obvious that you cannot do what the card is supposed to do at that moment.
Source: PUI Rules Team (2005-09-22)
If you use Rare Candy to evolve a Pokémon, and the evo card has a "Coming into Play" Pokémon Power (such as Dark Crobat), does that coming into play power get activated?
Using Powers, Attacks, or Trainers that let you put a Pokémon in the game from your hand will allow coming into play Powers to activate. This is a reversal from previous rulings.
Source: PUI Rules Team (2003-10-23), PUI Rules Team (2005-04-14)
Can I evolve Dratini in play to Dark Dragonite by using Rare Candy?
Yes. [This is true as long as there is a normal evolutionary path between the basic and the Stage 2 "Dark" Pokémon.]
Source: PUI Rules Team (2005-02-10)
Does Rare Candy override evolution-preventing effects such as Fossil Aerodactyl's "Prehistoric Power"?
Yes, you can use Rare Candy when Aerodactyl's Prehistoric Power is in play.
Source: PUI Rules Team (2003-09-18), PUI Rules Team (2004-07-22)
Can I use Junk Arm if there aren't any trainer cards already in the Discard Pile?
No, you cannot play Junk Arm unless there is at least one Trainer card other than Junk Arm already in the Discard Pile beforehand.
Source: PUI Rules Team (2010-12-09), PUI Rules Team (2004-06-16)
Can I use Rare Candy on a Pokémon that was devolved on that same turn (i.e. Devolution Spray, Hyper Devolution Spray, etc.)?
No, you cannot. A Pokemon must be in play since the beginning of the turn in which you are using Rare Candy. A devolved Pokemon counts as just coming into play.
Source: PUI Rules Team (2004-06-03), PUI Rules Team (2004-06-09)
The new modified rules state you may only retreat once per turn. If you use a trainer to Switch your Pokémon, can you still retreat that Pokémon? Or does the Switch count as your one retreat per turn?
Switch does not count as your one retreat per turn. If it did affect it, I would imagine it being written as "(This counts as retreating your Pokémon)".
Source: PUI Rules Team (2004-06-03)
If you use an Energy Search and don't find any Basic Energy, can you then play another Energy Search even though you know it will fail?
Yes, you can search for energy cards even if you know you won't find them. They exist as legal cards, therefore they can be searched for.
Source: PUI Rules Team (2004-01-15), PUI Rules Team (2004-01-22)
If you use an Energy Search and don't find any Basic Energy, do you still discard the Energy Search?
Yes, you would still discard it.
Source: PUI Rules Team (2004-01-15)