Unlike stocks, you can lose everything and then some, and then lose some more. 

I have a financial adviser but he's a stocks/bonds/etc. person, and I don't want to increase my holdings in that area of finance any further, so I don't really know what kind of person to look for, for advice of this nature.

No different than people who held stocks in 2008, if they sold when the market bottomed in 2009, they got clobbered, if they held, their investment is now worth even more than at the last peak ... and they've been collecting dividends the entire time.

I bought books on personal finance and the stock market, and on a whim I bought one of Brandon Turner's books on rental property investing, which led me here to biggerpockets.

I'll be putting some money towards investing, most likely in real estate, some in retirement/stock market through index funds.

I'd recommend the following ideas:1) If you can't find great deals right now, stockpile as much cash as you can and keep it ready for when the market turns a little south (this is the second longest bull market we have ever had for the stock market, so it will go down and pull housing with it a little).2) Try different approaches.

Instead they work for someone else, trade stocks/bonds on their own and are very good at what they do and enjoy it (read get paid well for their skills).I also know people who never have worked for someone else and make as much money as a doctor would at 30, running their own company, with zero debt or college education.Personally I’m somewhere in the middle.

The other thing I gleaned from this is its highly regionalized.. areas of older stock HIGH % of rentals wholesaling was much more viable.. areas of stability and owner occ and no boarded up homes much tougher. 

Don't wait because then you can be talked into waiting and waiting some more.Think about the same scenario in stocks, almost all stocks are bought and sold nowhere near the very top or bottom of their price ranges during even a week much less a year.  

I wouldn't borrow 100K at 5% to buy 100K of stock that I somehow knew was going to go up 5%.