I guess my main disconnect is that the market almost seems to be moving independent of the the actual COVID news. It's getting bought up when I can't see ACTUAL fundamentals returning to somewhat normal for at least 18 months.
JP Morgan just this morning said they see full asset price recovery in early 2021. I think Piper Jaffray called for new S&P highs by the end of the year! I know these are just opinions, but they are opinions of firms with thousands of analysts and extensive modeling capabilities.
I guess I don't see mainstreet America coming back anywhere near that quick. I'm not risk adverse by any means, but something makes me feel like this is all just a synthetic rally with no real reasons behind it. The bigger problem is that I *could* throw $200K+ plus of dry powder at this and potentially reap a very nice reward but my "gut" is giving me a stop sign.
My take - I
don't think you should throw your $200k+ dry powder at the markets.
You said: "That money will definitely need to be used early in retirement. I've always seen that as "safe" money and have let it sit in CD's (and I have flipped a couple houses with that money)".
This indicates to me that you should not invest that money in risky assets.
Right now, if that money is in a brokerage it is probably sweeped into a money market. This is not bad (please make sure it is in a good money market if this is not true).
You could further consider something like TIPS and such. Even bonds are "risky asset" (think bankruptcy) - so I'd be very careful and would likely avoid them in your position.
Beyond this position, however, I think every little scrap of extra money you can come up from your paychecks should probably be thrown into the risky-assets - with whatever asset allocation you desire. Now that we are all staying home - there should be some of that we should be able to find.
I, personally, stay in a much more aggressive investing posture. That's because I like my job (of being a code-slinging-cowboy solving cool business problems), and don't plan to RE even if I FI sometime soon. But, if I was looking to actually retire in 7-10 years - I guess my thinking would be different.
Whatever your decision is, however, please please please make sure you don't change that based on market conditions. Whether you take an aggressive stance or a conservative one - you should stay the course with that stance through all market conditions. Anything else and you are trying to market time - which almost never works over an investor's investing time-horizon.