@Aaron T.What is important is the nature of the investment, and short term rentals typically considered 'active' investments, especially given the fact that you run BNB business outside of your tax deferred account.

This helps address exactly what you seem to be worried about – that the folks investing the capital are getting adequate reward for the risk they're taking.As to your specific questions:1) No, I don't think it's selfish.

Rather than trying to time the market or find the "perfect investment", focus on finding a niche that's going to provide enough cash flow to support the kind of life you want, in a manner that supports the kind of life you want.Buy something that cash flows, with long term debt (10-30 year term, amortized over 25-30 years) that isn't over leveraged (LTV less than 75%) and have adequate cash reserves in case something goes wrong. 

If the answer to question #2 is yes, would it just be better to ditch the LLC and make sure we each have an adequate umbrella policy?

You fear because, right now, it is something you haven't done, so your lizard brain will naturally panic because it doesn't know what comes next. 

I did a few thousand of them for my clients. end of the day though its a max leverage minimal return game.. which if your up for that that's fine.. just make sure you have adequate reserves..

short answer is you don't get into them.you just have to walk around them and peer into the windows..if the windows are all closed up.. then that's tougher. many times a window will be left unlocked you can get in that way but its trespassing.many times as well a few days before the sale all of a sudden the back door has been kicked in.some investor ahead of you.. simply wont bid unless they get in side and they have kicked the back door in.ONe guy I knew was small of stature and could get in through doggie doors  LOL.but that's the nature of foreclosure business..

That is just the nature of the market right now.

Building teams and managing human capital is what I'm best at, so some of it is natural. 

Hope it works, but I plan for it not to also, based on the sketchy nature of craigslist.