...So for me portable means at this stage something I can take with me in the car/truck, this could be handheld or more stationary.
My goal is to be able to communicate with my family who are approx. 300 miles away. We have a good many mountains between here and the coast. Lets us a price range of 750 for now and see if anything comes close to my demands...
Let's back up and analyze the situation, and what bands would
provide a possible solution, before looking at specific radios.
The first distinction is VHF or HF ("short wave").
Depending on where you are in BC, you may have a linked
repeater system that would provide the desired coverage
using hand-held radios, although you may need a good
external antenna, depending on your location. That's
probably the minimal cost approach. But you will have
to check with the local radio club or other local hams to
see what the repeater coverage is in your area.
Now, while hand-held radios are popular for those who like
to tote them around on their belt, I find that a mobile radio
is much more useful. It can be mounted in the car, in the
house, or, if needed, operated portable with an external
battery if necessary. They have more power than hand-held
radios, and you don't have to worry about the battery packs
dying if they go too long without a charge (although any other
battery you use will require some maintenance and care).
And in difficult terrain, you'll probably want some sort of
external antenna to go with it.
Doesn't have to be an expensive radio - can be single band
(probably for 2m) if that is what the repeaters use. And,
while the newer radios often advertise higher output power,
I've been perfectly happy with 25 - 50 watts, and don't
see any advantage in going higher in most cases. (Improve
your antenna before raising the power.)
So that's VHF/UHF FM: may work great if you have the
repeater infrastructure to support your desired communications
in your area. Otherwise, can be somewhat limited, unless
you are on a hilltop.
The other option is HF ("shortwave") radios. These are capable
of talking around the world when the ionosphere is cooperating,
but out to 300 miles requires a different approach than longer
distances.
The lower HF bands, particular 40m and 80m, provide good
local coverage (less than 1000 km) when the ionospheric
conditions are appropriate. Sometimes you may need to
use 160m (which technically is an MF band, not HF), and
even then, coverage may drop out at night, especially in
winter at the bottom of the sunspot cycle.
The propagation mode is to send signals basically straight,
bouncing off the ionosphere, and back down. That means
that mountains aren't an impediment. However, antennas
are considerably larger - a dipole antenna for the 80m band
is a wire 40m long, although it doesn't need to be too high
off the ground (10m is quite sufficient, and 5m may be enough).
One problem with ionospheric modes is that the ionosphere
changes throughout the day / year / 11-year sunspot cycle,
so you need to be prepared to use different bands at different
times, and the stations you want to work will need to shift
accordingly. That requires some advance planning.
All of these methods require that the stations at both ends
be licensed, of course.
Now, another confusing point is that there are many different
definitions of "portable" operation. For some it means a
minimal station that can be carried in a backpack. Others may
include operating from a vehicle, or from a temporary station
at a summer cabin or campsite.
Most modern rigs run off 12V, so they can be used in a vehicle,
or operated from AC power. And we've come a long way since
the massive, heavy radios of the 1940s and 1950s. While there
are various "pocket-sized" radios running low power that are
great for backpacking, most normal-sized radios are quite
capable of being carried in a vehicle where space and weight
are not at a premium.
There may be other considerations: for example, how long the
radio will operate from a battery, or whether it is suitable for
digital communications (similar to email) or can be controlled by
a computer if desired.
So, before choosing a radio, you may want to look at what
frequencies you may want to use, and how you plan to use it.
Then consider what antennas you need to go with it, including
those for the stations you want to talk to (who may have
different constraints on antennas than you do).
I've done a lot of portable operation over the last 50 years,
in many different situations. When I started out I had a whole
footlocker full of radio equipment, and later lugged my old
tube/valve transceiver around with me to summer jobs and
out camping. Newer solid state radios are smaller and may be
lighter (depending on choice of power supply), but I still find
that most radios are suitable for some types of portable operation.
Unless you are carrying it in your hand or a backpack, choice
of radio model isn't as critical as understanding all the other
options and how to make use of them to achieve the desired
communications.