From much experience using HT's in hospital support environments, use an earphone directly. Speak into the HT mike directly. Better ransmitted fidelity, and the earphone will keep from distracting everyone around you. Do not put the HT into a pouch or on your belt, your body will absorb the RF, and you won't communicate as well. The rat tail (counterpoise) can help on 2m, but you'll rarely need it. 440 gets around inside buildings much better than 2m does, and the counterpoise doesn't make as much difference on 440 as it does on 2m. If you use a really long antenna on the HT, you're likely to poke someone in the eye with it. Go with something under a foot long if indoors!
If you need to monitor two frequencies, use a separate HT for each frequency, with separate earphones, or use earphone on busiest channel, leave the other channel on speaker. With an HT that can receive two freqs at once, if one channel is busy, you won't hear ANY calls on the secondary channel. If you need to tie into an antenna outside the building, bring a diplexer so you can connect both HT's to the external antenna.
(lessons learned from training by and experience with the Hospital Disaster Support Communications System (www.hdscs.org
Fred Wagner, KQ6Q