Oh trust me Greg, you aren't telling me anything I haven't already heard before. I know that you started this thread to help newbies understand and get acquainted with investing in the market, but I can't help wonder if it can't help disillusioned investors as well.
I've tracked all of my investments in Quicken and I haven't put Quicken back on my home laptop since it's hard drive crashed last summer. When I get to work tomorrow I can give you some examples of equities that worked out well for us over the years and some that didn't even though I held them much longer than I should have. The tax free munis were not in my retirement accounts, they were in the taxable accounts and yes, they were used more to keep taxable income low than capital appreciation. They were supposed to be the "safe" investment for my more liquid assets.
Dollar cost averaging, keeping on buying even during the 3 different bust periods we've been through, was really what saved us. I understand that theory very well, just as much as dividend reinvestment which we've also always done. Problem comes when there's no more income coming in to keep on pouring into the market during the down years.
My FA is not a pump and dump type of guy and if we moved in and out of certain stocks or asset classes at the wrong times, it was more likely at my doing than his. I'd say over all we were about 50/50 on moves working out, half real good, half bad timing, but there were other factors involved as well in those moves, not just trying to market time.
About 1 year after I cashed out, I plugged into a spreadsheet all of the investments I held at the time and updated the share prices. This would have been approximately August 2011 - August 2012. The total appreciation was about $10,000 and about half of that was in Apple, which I would have probably sold before then as it had had a huge run up during that period. I realize that dividends wouldn't have been included in that calculation but the dividends were pretty small scale on the grand scheme. I just used this exercise to try to see what I missed. I came away from the exercise thinking that the extra sleep I gained during the same time period more than made up for the gains I missed out on.
I think mentally, if I'm going to get back into the market, I'm going to have to ease back in and only with a set percentage of the overall. When I was in before, I had 90% or so of my liquid assets invested. It's very unnerving when your business is taking a dive and at the same time your net worth is taking a dive as the market crashes. Tie into that some untimely deaths of friends and family members at near the same time and it makes one step back and reevaluate exactly what is most important.
My wife and I have spent the last 20 some years working our tails off and saving and scrimping and making smart financial decisions at the cost of personal enjoyment. Everyone has to decide for themselves when enough is enough, and I don't know that anyone will ever really know. I know this though, I'm going to stop chasing every last dollar I can and start taking the time to spend with those I love and enjoying day to day. If I have to adjust my life style in order to accomplish that, I'm okay with that. I spent a lot of years with nothing, so I know how to live on very little if necessary.
I do realize that I need to do something to keep up with inflation though, and that's what I'm trying to figure out how to do while preserving capital at the same time.
Please don't take my posts here as an anti-Greg investment theory stance, I don't mean that in anyway whatsoever. I'm intrigued by the way you describe your investing and am thankful that you are so willing to share it with others. Much like Ron has helped me dial in the tuning on my car, I think it is very cool that you give back your knowledge free of charge to anyone that will listen. I'm just trying to figure out if there is a way to make it apply to my personal situation comfortably.