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Live-in's mom does rent-to-own with her house, but she's only 20 minutes away. It's worked out well for her (at least in terms of having stable tenants for the last two years), but please remember that just because you do a rent-to-own does not mean that the tenant HAS to buy the house at the end of the terms of the agreement. She's facing that predicament herself now, and doesn't know if they'll end up actually buying. True, they've paid more in rent than they would have if they just rented it without a rent-to-own, and she gets to keep that if they break the agreement, but she'll still end up with a house that's just too big for her to live in alone, and hasn't been able to sell and get what she owes out of it.
A pro of renting-to-own is that the tenants (at least at first) tend to care a little more about the house and take better care of it. Live-in's mom's tenants actually did a lot of landscaping work, painting, sprucing, etc., and the house looks great. She's only replaced the washer and dryer for them since they moved in.
For caretaking, if you have family in the area you might be able to make it work if you make an agreement with them in advance of signing a lease/rent-to-own agreement with a tenant. You may also consider contacting a caretaking service.
I would suggest contacting a realtor about the ins-and-outs of renting v. selling v. rent-to-own.
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