@Shane Kelley VRs are definitely a niche strategy. I think many people start as they would in standard SFR's - at the lower end and then work their way up. In the VR market, this equates to condos.
I would urge anyone to take a hard look at the numbers of condos (Hint: HOA fees) and recognize that it's difficult to build up a loyal customer base as a condo VR owner since most travelers have an affinity for the community itself - not your individual unit. I think partnering on a larger primo beach-front VR is a better choice, over picking up a condo only to break even indefinitely.
I have an SFH that we use as a VR. It cashflows on par with an SFR, but I would argue there's far more appreciation potential. The tradeoffs for this advantage are:
1) Involvement. It's far less passive than a standard SFR. I liken my position to one part landlord, one part tour guide/insider, one part concierge service.
2) Risk. It's a feast or famine niche. The next storm, economic downturn, oil spill, or Zikapocolypse will signal a steep decline in VR demand. That downtick could be short or prolonged, localized or global.
3. Expenses. VRs are more expensive to operate. People expect a perfect house - spick and span without any loose doorknobs, creeky doors, stained carpet or any other ideosyncracies. Additionally, there are many more items requiring maintenance: full furnishings, appliances, amenities, etc. Don't forget utilities, including cable. I did a lengthy post on expenses a bit ago that provides some insight.
Bottom line: If you're a straight cash-flow investor, VRs aren't likely a magic investment. If you're after appreciation, they likely have an edge.
I personally enjoy it, but that's because I enjoy the tourism market. (But there are weeks like the one I'm having: Current tenant overflowed the upstairs bathtub. I've got ~30 hours after they vacate to sheetrock, tape & repaint my living room ceiling before a wedding party checks in!)