There would definitely be a knowledge gap in switching/adding something new to your portfolio, and bigger gambles could mean bigger losses in the event of a mistake while learning. 

Those both seem rather big gambles as opposed to hedges... but hey, each unto their own. 

Even when young and could not really afford it, I would not hesitate to buy a new car, knowing full well that financially it was a bad deal.Taking a risk on a RE investment was just too much of a gamble - why, because it was different, it was not the norm, that made it scary.Even when I had plenty of capital to back me up, it was still difficult to make the first buy.I still suffer from analysis paralysis when looking at properties - that's probably due to some fear still existing.I'm still a relative newbie in the REI world, but every day it's becoming a little less scary.

Owning a property for a year is a tough gamble, since you pay a lot in selling commissions, etc so breaking even is tough. 

Here is my response to that question:I don't go to casinos to gamble.

Now, if you want to gamble a bit 'cause it's really a nice place, I'll buy the place subject to at a higher price, if ole Boyd gets to closing on time as agreed under the option, well, I lose the premium I paid and I'll need to sell it to him at that price....but, if he fails to the second (be'n the good ole boy he is) then I just keep the place and he'll need that stool.Fausto, not so close to Wayne, he'll get splattered, little more back towards you....that's good, right there, KA DING thanks.Speak'n of ole Wayne, he's on to someth'n there, a good Option Contract IS a purchase contract, in fact, you can go by a purchase contract and just take out all that default malarkey that nails the buyer if'n they don't buy the place.

Naperville is a good place to buy and hold for appreciation but personally I think of that strategy as gambling.

The point is, it's a gamble.

Somewhat of a gamble...2.

But buying at retail value simply based on the hope that values will continue to rise is like gambling.