Like a lot of us, I started off with HTs....an Alinco DJ-C5 (2m 70cm 300mW) because it was insanely small and cute (it's low power wasn't a huge issue when portable because our area have a lot of repeaters) and almost immediately a Yaesu VX-5 (5w 2m/70cm/6m) because the aliinco was nearly useless in a car.
The VX-5 did sort of work in the car, but even with a speaker-mic it was cumbersome and difficult to hear. And by the time you connected/disconneced a speaker-mic, and extrenal antenna and external power...well..."handi" wasn't a good word to describe it.
I *did* manage to get a few sat contacts with it, after I borowed an Arrow antenna. As others here have observed, working sats without full-duplex (rare in an HT) is very tricky,
But I didn't have my ticket for long before stepping up to a Yaesu FT-90 (50w mobile 2m 70cm) in the car. And when I upgraded to Extra and got HF privileges, I went straight to a Yaesu FT-847, which is still in my shack today. This all happened in about the space of less than a year.
(Of course none of these radios is in production today...but there are some near equivalents.)
I guess what I'm saying is: don't kill yourself trying to get a lot of features on an HT that doesn't have the size or power budget to support them, since you're likely to be stepping up to something bigger sooner than you may think.
-- 73 de Maggie K3XS Editor, Phil-Mont Mobile Radio Club Blurb - http://www.phil-mont.org Elecraft K2 #1641 -- AOPA 925383 -- ARRL 39280