@Natalie Davidson I should have clarified that more. The rental market around here is much more likely to fluctuate in bigger swings with our snowbirds and students than the sales market. I've had much better 'luck' finding things I am interested in purchasing here in St Pete from off market deals than what's on the MLS.
A quick search today shows 203 SFH on the market in Pinellas county with a min 3/2 priced 80-120K. Knock out the short sales that are under contract and you're down to 136. Knock out for more features/neighborhoods/repairs you want or don't want until you get down to 20 or so and what have you got? 20 properties priced at higher than retail in spite of at least 10 of those having recent price reductions of 5% or more off their most recent list price.
Pull up the number of closed sales for the last 6 months in the county with list price between 80-120, 3/2 and there were 699. So basically you're got one month's worth of inventory on the market and anything that's been sitting generally has problems that most folks don't want to deal with or the price is just way too high. It's been like that for the past year and half regardless of the season.
I'm glad to see the retail houses selling to the retail buyers at retail prices again. But a lot of the fixer uppers that have traditionally been the bread and butter properties for buy and hold (and stuff you get emailed from the local wholesalers) makes me want to tell them to quit hitting the crack pipe before posting. Yes, House A could be just as nice as House B once the repairs are done - but that doesn't mean anyone should pay just $5K less for House A and spend another 30-40K in repairs just because someone has learned how to make a pro-forma look pretty. There's not much inventory and there's even more junk to sift out than ever - it is not a pretty cool lake for a newbie to learn to swim in; there's a lot going on just below the surface.
You didn't really specify what your investment criteria are - but that needs to be clarified down to a standard measurement that you use to evaluate any and all properties that you find interesting. I just closed on a duplex that I got for 40% of list price. But that wasn't the deal. In reality what I got was a duplex with an unlicensed 3rd unit for 15% less than it appraised for as a duplex on a zero down loan at 4.375% fixed for 30 years that provides me a place to live and throws off $200+ per door while I go through the hoops to get the 3rd unit legal. It worked out for me because the agent had it so overpriced that no one who would have been seriously interested in it bothered to look very closely.
Which goes full circle back to my original reply:
"The best time is the day you find a motivated seller that wants to get rid of a property that meets your investing criteria. Anything lacking that just isn't a good deal no matter when it's on the market."
It's way more important that you define what a good deal is for you and go find that than any time of year. Happy hunting