Smart money is on the sidelines. 

After years of analysis paralysis and watching from the sidelines, we finally had an offer accepted on our first STR property in the mountains of Vermont.

It just seems more obtainable since we don't have a lot of money on the sidelines currently.

But if I have $50,000 sitting on the sidelines I am not putting it in life insurance only to pay to borrow against it. 

Not really a big business, but a good supplemental side line at home.You will have issues and upkeep with your dump station.

I know that it is impossible to answer that question without detailed numbers, but my general question is how do you balance being selective and waiting for a great deal (but having your money on the sidelines) with the advantage of putting your money to work for you sooner on a good (but not great)  deal?  

The whole concept of going in on a multi-family property and agreeing to balloon payments has me a bit sidelined on the idea to be honest....

None of us want to speculate into the up market, but that means we'll be sitting on the sidelines potentially for years.  

@Christina TraffanstedtI echo what others have mentioned - spend a couple of months on the sidelines as you repair your credit scores.

Now, the notion of sitting on the sidelines bitting one's fingers in expectation of this "proverbial crash" is detrimental to wealth creation.