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I've thought about it too, and know someone who has, but there are some logistics:
1). Physical seperation of the house: Optimally there would be two staircases/entrances so you can enjoy personal time(without someone walking around looking for the bathroom) when the service bell isn't ringing, while having someone keeping track of the grounds.
Sometimes it helps to think like a traveller-are the bathrooms and kitchen accessable etc...?
2). Money transactions: Being able to check and process currency and credentials from international guests. Some of these people will be tired freaks(!!!), but some will be fascinating story tellers that will keep you entertained to the wee hours.
3). Business plan/profit vs. investment: In down times there is a reduction in travel, and the area has to have a constant/seasonal draw for people with travel money. Big cities near convention centers/museums/etc. are good, so are tropical paradises.
4). Division of labor, and variables: There will be daily bedsheets and vacuuming to do. Trustworthy help is a must, and the business and your back depends on it.
5). Probably second most important-Advertising: Where, when, how, how much.
6). Most important-Self realization: Now this business is up and running enough, you are stuck doing the same old things, and answering the same old questions year after year...are you happy? Does peak season interfere with track season? Important to think about now.
Reading your posts I think you'll do fine in whatever you choose.
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