You can spend as much (thousands and thousands) or as litlte (nothing to a handful of dollars) as you want.
NYCFireFighter, given your forum handle - if you are in the NYC area and not Texas as your location suggests - maybe you can make inquiries of your radio shop - perhaps they have a line on surplus commercial gear that can be repurposed for use on amateur frequencies. You might be able to use an old but well built brick of a radio for next to nothing.
Clubs affiliated with cities are also good sources of surplus gear; they can also be good organizations to check into for advise, ham to ham sales of gear, and fun of course.
Some older amateur gear holds up very well over the years, particularly VHF and UHF mobile units. I'm still running an ICOM IC-901 I bought decades ago and it doesn't even look like "old" tech.
Part of the challenge is figuring out what is interesting to you. If you aren't sure, and are not yet licensed for HF, then usually FM voice on VHF or UHF is a safe bet as a starting point.
If you already have some local ham friends, or are looking to make some local new amateur radio friends while commuting to work, often a 2M VHF FM portable or mobile radio will deliver useful service. In some cities or regions, 440MHz (70cm) FM or 220 MHz is also popular - check around locally before spending money.
Many areas are serviced by repeater systems that are linked together using something called IRLP; to use these systems usually you need nothing more than an average handheld (or mobile) radio and occasionally some way of keying in a DTMF ('touchtone (tm)") code to bring up or down some other repeater on the network across the state or country or world. Some digital systems require more of an investment - such as the ICOM DStar system, or the commercial radio based ham deployments of DMR (Motorola, Vertex, Hytera - but mostly Motorola gear in use). Yaesu is rounding out their product line but being so new, few are using it broadly. Unlike analogue FM radio, digital voice/data over FM radio requires specific, compatible, equipment. Definitely talk to the locals before spending money in these areas.
Wherever you live, check with one or more of your local clubs and try to find a local plugged-in ham to give you the lay of the land. The advice you get might save some time and $$ too!
73
Mike
VE7WV