From Colorado - Looking for Coastal STR - Oregon Florida SC Cali

[Matthew W.]

Hello! We love our home state of Colorado, but we're eyeballing the ambitious project of acquiring our first real estate property as a family vacation home which can successfully operate as a short-term vacation rental when not in use by us. My wife and I would like a bit of ocean breeze and fresh seafood in our lives, but we want to be smart about how we pursue it...

I'm aware that we need to do a lot of number-crunching, local contact development, and research into local STR regulations, but we're actually struggling with the broader question of -= WHICH MARKET? =- Input is welcome... we are flexible as to condo/townhouse or SFR.

Oregon is a quick flight from Colorado and in general, a good hub for our relatives to gather as a kind of family reunion spot. However, I've seen a lot of posts here and elsewhere which suggest that its shorter summer season makes a coastal Oregonian rental property struggle to get year-round revenue. Although we want a place convenient for us, we don't want to ignore the financial calculus, as this is meant to be a profitable springboard to more real estate investments..

Hilton Head Island and Myrtle Beach are interesting as beach destinations which don't typically receive hurricane activity, but do get considerable tourist traffic. HHI seems more ritzy and hostile to STRs, while Myrtle seems more receptive to them if perhaps less glamorous than HHI.

Florida.... I have never visited Florida and have really no idea how to invest here. The prospect of doing so is intimidating, but blogs and articles re:  vacation rentals overwhelming support the profitability of Florida.  If Florida is really a vacation rental gold mine, we'd consider it, but the plane flight is starting to get pretty long with kids. Also, hurricanes seem to whack it every 5 minutes.

California - REI blogs and forums seem to strongly disfavor this, presumably because of the high property purchase price and already-high presence of retail hotel/motel chains, and competition keeps avg daily prices modest... San Clemente caught my eye when visiting as a slightly cheaper SoCal area to buy property, but I am not sure if California is even worth investigating heavily because of the aforementioned concerns...

If you think there is another beachfront market we're completely missing or one that is likely to boom in the coming years, please chime in.. :)