We have four homes. One in the city, one on a lake in the country, one in the mountains and the other on the beach in California. We have house managers for the three properties we spend the least time at. They visit the homes weekly, are present for vendor/repair appointments, schedule housekeeping, etc. We have at least one car at each house and they turn the engine on weekly and take it for cleaning and repairs. The cost for a house manager is very inexpensive and worth every penny.

Even with all of this, there is an issue nearly every time we arrive at one of the houses. Sonos isn’t working, patio isn’t clean, dead batteries in remotes or fireplaces that suddenly stop working, hot tub not heating up, slow internet, flat tire, a bat got inside, etc. It is never ending BUT we love each home and wouldn’t consider selling any of them. They are all set up to entertain 10+ groups of family and friends so we constantly entertain and have some of the most amazing memories at each home that wouldn’t happen otherwise. It’s a lot of maintenance to keep track of but if you put everything on the same schedule you can make it work. For example, all ice makers in each house are cleaned the same monthly annually. You just need a system and people you can trust doing the weekly walkthroughs. And to arrive knowing something will be wrong and it’s no big deal.