Buy once; cry once when it comes to electronic tools.
A good DMM and soldering iron plus a technician's tool kit (screwdrivers, cutters, stripping tools, crimpers, soldering aids) will definitely be on your short list to get.
My test lab is a little more comprehensive since I do design and mod work as a counterpart to my day job. See if you enjoy the hobby enough to invest in additional test equipment then I'll/we'll help spend your money.
Radios - all in what you're looking to do. For a general-purpose multiband handheld which is also waterproof (literally), I highly recommend the Yaesu VX6, VX7 or VX8 series. Kenwood's TH6FA is also another good choice, albeit not waterproof.
Mobiles and fixed-station rigs open up an entirely new can o' worms...and will get some interesting discussions raging about what's "best".