I don't know pricing in Canada, but the safest cheap Fluke for voltage measurement is the Fluke 101, (partly because it doesn't have current ranges) and the lowest cost reasonable DC current clamp, the Uni-T UT210E (lots of threads here). I'll leave you to do the costings to see how that works out against alternatives. There are also other low cost Flukes (11x family) but price climbs fairly steeply.
I'll have to leave it to you to decide how competent you are to work on mains, and mains SMPSs in particular - things can go South very fast! If it's something that you are not realistically going to do, then you can save (everything?) on DMM cost.
I would allocate as much of your budget as possible to the scope. Lowest cost decent benchtop units you might consider are the Hantek DSO2C10 (a few bugs but mostly perfectly fine, see DSO2xxx forum threads) and the Rigol DS1102Z-E, again you need to look at local pricing but the Rigol is getting cheaper with the newer ranges coming out.
I know you have a crap (USB?) 20MHz scope, but a USB scope you might consider is the VDS1022I. I know it's only 2 channel 25MHZ (~30MHz -3db) 2x 100Msps, but it does exactly what it says on the tin (unlike the Hantek and other cheap USB scopes), has decent PC screen update and has galvanic USB isolation (to protect your USB port, not for mains isolation). There is also an alternative, improved, PC app for it. Again check pricing (make sure it's the 'I' isolated version) and forum threads. Just a though on this one anyway, it will be cheaper than anything else you are considering.
P.S. Check out the Owon handheld scopes too, eg the HDS272, they are much better than the Hanteks in side by side comparison videos.