they bought like 1,300 houses, keep them for years, then sold at a big profit at peak of market. 

Bye.

In fact, I have brought most of my properties on board at the beginning of the peak season or right before.

With short sales it is a waste of time going back and forth with a seller to get to a price only to have to do it again with the bank on the loan and all other junior lien holders.What you want is a pre-approved short sale.Someone else has already gone through the pain and anguish of submitting the offer and getting the price approved and are usually long gone when the bank gets back to them.You come in at the right time and strike a deal with the least amount of hassle.This is also important because during the initial contact with the bank on the short sale it could take weeks or months to get an answer.You go under contract for say 130,000 when it's listed for 140,000 subject to bank approval.2 months go by and the market has dropped down another 10,000 in values when you get a response.They have a high BPO from the bank and the bank wants 135,000.Now you are looking at a 15,000 gap with the market diving down.Now the bank wants to order yet another BPO which takes more time and the market goes down again.They are better with short sales now but a few years ago some would take 6 months to a year to happen.Great if the market goes up but not if the market goes down during that time as your contract price will be inflated.If the property is pre-approved and the price is great short sales are worth it.If not there are too many other properties to look at.Just tell the listing agent that is as high as you want to go and have others you are bidding on.Say if you want to get paid I am a serious buyer so see if you can make the bank accept the offer.If they really have another offer they will tell you bye,bye.If you are the only game in town and they were bluffing they will try to push it hard.Unlike an REO listing agent the agent is not getting more listings from that client on a short sale.The best they can get is a referral from their client they did a short sale on.Not many people say "Hey this agent did a short sale on my house and it was great and you should use them if you can't pay your mortgage".Most will want to keep stuff like that private.

Of course, if we do that, we can kiss any chance of financial freedom good bye...

Seth B. Yes

Most people don't peak behind the blinds. 

I do not want to be getting the property back in November and risk 3 to 4 months of vacancy during the off peak period.  

If you are in an area of harsh, cold , winter months make sure the end of your lease does not happen at the same time.It will be very hard to rent.So If you didn't like them and the lease was set to expire at an off peak market leasing time you might want to get rid of them now.

So of the bat , answer is no.Correction 10% .. answer is depends on the property.Single family.. noApts, condo, multi.. yes yes.Inventory to come back June afterwards, September should be the peak .Buyer demand remains low for non SFH.