@Troy Hebert your post resonates strong with me! And your concerns are primarily what has kept me out of RE for these last few years as I've learned more and more about it. (I'm actually about to go full throttle into RE, but that's for another time.)
Why should I invest in an illiquid, risky asset when I can get better returns in the stock market? And to get the type of returns that make it worth it, I'd need to pour hours and hours into it - at that rate, I can get another job which could pay as much as a return on a small investment property.
If you want to get into RE, the way I see it, you have two options. The first is easier, if you're trusting of other people. Partner with others who will do the active management (including rehab, mgt, maybe even deal sourcing). This can be through any of the million syndicators out there or a friend/business associate who you trust that is involved or wants to get into it.
The other option is to go searching yourself. You have to commit to looking at deals until you find one that suits you. Literally, you cannot stop until you actually find something. Because otherwise you may spend months looking at dozens if not hundreds of deals which are not good enough for you - only to quit. And then you wasted all that time. If you commit and push through until you close on something, retroactively all that time "wasted" becomes part of the process, which it is. Ask any seasoned investor and they will tell you that finding a good deal is only a matter of pushing through until you find one.
The high IRRs you hear about are partially due to capital appreciation, but more directly, usually a function of improved property performance. If I can improve the NOI, my IRR can go up significantly. Now that my property is worth more because it is shooting off more income (on larger multi-family and commercial, value is strongly related to NOI - hence, you can significantly effect capital appreciation with minimal broad market influence), I can further raise the IRR by cashing out a refi or selling for nice profit. But again, you either need to commit to scouring the planet until you find something or partner with someone/company that's already doing this.
As far as market timing goes, just be conservative when you underwrite your deals. If you project that in a downturn, your expenses can withstand a drop in rent, so you're protected. One thing that was not mentioned was that if you end up in a larger property with a commercial mortgage, they're typically 5-10 year loans with 20-30 year amortizations. If your property loses value when your loan comes due, you may have a significant challenge refinancing, unless you have a ton of equity that you (temporarily) lose.
Best of luck and keep us posted on your decision and journey!