This should become a popular thread...
I managed for years and years with ordinary planes, some bought second hand and some from Dad. Then when the Parf Dogs got going I invested in Veritas planes and my life at the bench changed over night. I have 3 low angle models - Jack, Smoothing and Block - and all are brilliant.
As a non commercial woodworker it is hard to justify any large machinery but I could not manage without the Jet JPT260 planer/thicknesser. It was not cheap but I believe it to be excellent value for money.
Over the last 7 years Axminster have really improved the quality of tools sold under their own brands (Axminster and UJK) and some of these are worth a mention. My Axminster bandsaw cuts architectural veneers beautifully true. I am just getting into their Centrotec ended drills and screw bits and these are very good too.
Measuring and marking is a vital area and I would not wish to be without my Incra Precision T Rule which I bought from The Woodworkers' Workshop in UK. I use engineers' squares in the workshop as it is so very hard to find a "woodworking" square that is accurate enough. Buying tape rules and steel rules is a bit of a lottery and it is best to establish one that you know is spot on and then take it with you when you buy any more. I have a Rabone Chesterman 600 mm steel rule which I know is accurate and I use it as my reference. I have recently received a sample of a new 610 mm steel rule from Axminster which is also spot on and has the advantage of left to right and centre outwards scales - ideal for getting drawer handles centred.
Although not in the aim of the OP can I just say how valuable the various tool shows and demo days are that we have access to in the UK (and I am sure that this is true for other countries as well). These are really well supported by the manufacturers and the suppliers and provide an invaluable opportunity to see tools in action. It really helps with the decision making process. Family run businesses like Lee Valley, D&M, Toolfest and Axminster (I know that there are many others equally as good) do a lot to help as well.
[I managed that without saying "Festool" at all. My stars are - Domino, Kapex, CT26, TS55, OF1400 - sorry !]