So I'm fortunate enough to have the money to own two properties. So I want to know:
For those of you live in two places.
a) What locations and what months? Why did you choose them as a pair.
b) What are some of the hidden issues you didn't foresee?
c) Any other tips/suggestions for people researching two areas to live in
a) northern Michigan and west-central Florida. The Michigan location is where I spent most of my career, and I lived year-round here for 50+ years. Still live here for 7 months of the year. Once I retired, we started looking for warmer spot to spend the winter months, and settled on west-central Florida, after spending time in a couple different spots (Florida Panhandle, Texas).
b) no huge surprises or big hidden issues (so far....we've owned the Florida house for 2 1/2 years).
c) well, the obvious suggestion is to own homes in very different climates, so you can spend most of the year in a place where the weather is pretty nice. That was our main motivation for buying the place in Florida.
It is true that you will need to figure out what items you can just bring back and forth, and what items you will want to keep at each place. After we bought the Florida house, we filled a U-Haul trailer with stuff to bring down there from Michigan (mostly tools, my fishing gear, some clothes, etc). Since then, we only bring things back and forth that will fit in our pickup truck. It has worked out okay, for the most part. As far as outfitting the house with kitchen stuff, furniture, tv, etc..........we just bought all that stuff down there, mostly used stuff in good condition so it did not cost us all that much.
So far, it has worked out pretty well, and we have no regrets. We do rent the house out during the summer months when we are not there. The key to that is having an excellent property manager, that lives close-by. Fortunately, a neighbor of ours does that job for us, and he does a great job. We have another guy that takes care of the grass and other small yard chores, and he is reliable also.