@Eric Petersen
Hey Eric, Any news on your efforts?
A bit late to this one, but started looking into vacation rentals myself again. From what I have seen with close acquaintances' ownership of duplex in Breckenridge, the high season can make up for the lull of pricing and increased vacancies in the shoulder seasons. The way they have made the rental work is with a good email list of previous renters and a good presence on social media, offering variably discounted rates dependent upon demand and last minute deals to previous renters.
As @Kent Verge mentioned, getting out of those 'rental communities' is what seems to make VRs work, and tying a long term renter to it... all the better, very nice platform Kent (maybe have that long term renter manage the short term rental as well?)
One of the partners is a software developer and has everything automated in terms of calculating demand and discount rates, as well as emailing previous renters. He built in automated emails to cleaners, pool guys, and renters, so management has become minimal.