Ragoo said:
My parents have one they strictly rent out, used to have a second in the same complex. They bought both via foreclosure and did rehab themselves. They also manage the property themselves and list on vrbo and similar.
Otherwise it is barely a break even proposition.
My aunt/uncle owned a couple condos in Vail. For years, they profited largely as it rented most of the year for good money. It paid it's own mortgage, plus the mortgage of the second one they owned and used ~30-40 weekends a year.
But, one year, the association made it to where they would no longer allow VRBO or any type of personal listings, and that all rental must go through the association, and alas, pay 35%. This made it unprofitable/break even. They ended up upgrading it and selling. The profit on the sale paid off the mortgage to the one they still own, so they still made out really well.
We are considering buying a condo in Breckenridge, where we also have a time share at a ski in/skit out resort. We would rent it the bulk of the year, but I will make sure that I am allowed to personally list it, and not be required to go through the association. With our benefits of day use at our timeshare (park in the heated garage, use the ski lockers/pools, ski in/out, etc), it would make for easy skiing.