I love my Simpson 260's (I have two).  They typically sell for about $40 at hamfests.  Several series, I think latest is 7 or 8.  There are always a bunch for sale on eBay.  I would lean towards a series 6 or 7.   Here is a current example: 

http://www.ebay.com/itm/Simpson-260-Multimeter-Series-6-/281011726788?pt=LH_DefaultDomain_0&hash=item416d9aa9c4

I also have several digital meters.  All from Harbor Freight.  Some were the give-away models, great for throwing into a tool box, taking out to Field Day, etc.  Also have a couple of their better meters, regular prices of $40 or so, sometimes half price.  They really seem to work well.  Here is link to one of the meters I use.  I like the rubbery outside sheath for protection.

http://www.harborfreight.com/general-merch/electrical/ac-dc-digital-multimeter-37772.html

I have a Tektronix 2465B dual 400Mhz scope that I purchased several years ago for about $250.  Super scope.  Most any of the Tektronix scopes would be good.  However they all use proprietary solid state devices that are not available.  So if something fails, it is highly likely that the scope is unrepairable.  I have seen some new scopes (from China) for sale, in the range of $100 to $150.  Don't have any experience with them, but the specs look rather good.

Re probes, you can get a couple of 100Mhz probes on eBay for about $10.  I have these and they work great.  400Mhz probes are MUCH more expensive, and not recommended unless you need the extra bandwidth.

I use DXWatch on my PC's and laptop  For some reason, on my main PC (Win7), DXWatch suddenly stopped listing the calls.  The page comes up, but no calls.  My other PC is working fine with DXWatch, so I have to assume the problem has to do with some setting or change on the PC.  I seem to recall that I had this problem a year or two ago, but don't remember solution.  Any ideas?

This weekend is the biggest SSB contest, world wide, in the entire year.  So phone portions of bands will be filled to overflowing.  Not the time to expect "ordinary" ability to operate SSB.  CW should still be fairly normal (until the CW version of the contest).  Seems to me that your newish ham experience might be similar to a newer driver who has been driving around during mid day, or SUnday morning, and suddenly takes a drive during the peak of rush hour. 

The phone segments are crammed because this is a big deal to a lot of hams.  Will return to normal this evening.  Work some CW, if you know code, watch some TV, or take a walk, let the blood pressure drop.  Don't give up on ham radio, or contesters.

Not a direct answer to your vertical antenna question, but...

At my Colorado location in the mountains, I have four long-wire (about 180ft each) wires coming together at a tree. I use as V beams.  Ends of wires are in trees.  I have three four-foot bungee cords at ends of each wire (in parallel).  The wires have been up for 8 years.  Very frequently have winds of 60 mph and higher.  Never had a wire come down.  Last year we had 140 mph (!!) winds, knocked down tens of thousands of big trees in the area.  The only wire of the four that went down, was connected to a 100ft tree which was blown over.  The bungee cords really work to handle the tree sway.

Most of the members of the Kansas City DX Club have 1x2's.  Working DX, the shorter the call, the fewer letter that have to be copied or figured out.  I like to contest, so my 1x2 (vanity) takes less time.  I switched back in 2003 when I got active again.  My prior call was KØLMZ, but being inactive so long, it had no particular recognition to anyone but me.  So I didn't mind switching.  Not sure if I would have otherwise. 

I second the above recommendation re whole house (ie service panel) device.  Several types, but one common one plugs in like a two-phase circuit breaker.   

I have several of the cheapo Harbor Freight meters.  They work fine for almost everything.  Harbor Freight frequently has a free coupon for the meter.  Can't beat free.  Eventually I would recommend looking for a modestly priced analog (meter type) VOM to supplement the digital.   If you can find a good used Simpson 260 for under $40, that is good value.  Some uses for a VOM, the analog is easier to use since you can see the meter move.

The way I figure it re OQRS, it costs money to print and mail the card, and a cost for Paypal.  So something like $1.50 or so direct cost.  A $5 total helps maybe $3.50 towards the DXPedition.  Not big bucks, but helpful.  So, being retired, my personal minimum is $5.  I go to $10 if the DXPedition is one of those higher cost trips.   I also contribute $50 per year to Northern Calif DX Foundation for their support of DXPeditions.

Worked 2050 UTC 20SSB from Colorado.  One op was up 14160-170, next op 14150-170.  Both moving around alot.

Thanks.  No, I was tied up at that time, so didn't try.  Checking now 1957 UTC.

Best time for me in Colorado on 20SSB is 0030 to 0130 UTC per HamCap.  Nil until about 0000.  But operator QSY's each day to 40M about 2120 UTC.   Won't work many NA western side on 20 that way.  Bummer.

Not approved for DXCC (yet), but interesting.  Now on the air.  Here's a link to info.

http://www.arrl.org/news/a-first-hand-look-at-the-z60k-activation-in-kosovo

Another source for a dummy load eBay.  Fairly often I see used Bird dummy loads for sale at very good prices.  Hi wattage capability, usually flat to 1 or 2GHz.  My 500 watt Bird will handle 3KW for several minutes!  Heres one for sale right now:  

http://www.ebay.com/itm/BIRD-TERMALINE-COAXIAL-RESISTOR-82A-DUMMY-LOAD-BARKER-WILLIAMSON-500W-51-5-OHMS-/120992476639?pt=LH_DefaultDomain_0&hash=item1c2bb6addf

Another type on eBay are the 50 or 100 watt loads with heat sinks.  These go for very reasonable prices.  I have a couple and they seem to work very well up into the UHF range.  Here's a couple of examples.  Both are used but I see new ones quite frequently:

http://www.ebay.com/itm/RF-Dummy-Load-N-type-100w-4Ghz-50ohm-58B83464r01-/251160836782?pt=LH_DefaultDomain_0&hash=item3a7a5a3aae

http://www.ebay.com/itm/DECIBEL-PROUCTS-DB4303B-CONTINUOUS-DUTY-100-WATT-100W-RF-DRY-DUMMY-LOAD-N-MALE-/221117414756?pt=US_Radio_Comm_Antennas&hash=item337b9ffd64

I don't have any model Flex, but do find their demo's at Dayton to be quite interesting.  However, I found long ago never to buy version 1.0 of any software, to wait one year when a car is completely redesigned, and to wait at least six months before buying any ham hardware.  No matter how good the engineering, there are always a few bugs and possible improvements.  Following that logic (and experience), it doesn't make sense to me to give a deposit on what might easily be a "beta" radio.   John.