Greetings:

 I've built up a pretty successful computer consulting business in lower New York.
 However, as much as I like New York, I hate the winter weather,
 and have thought about expanding my business to another area, most likely
 Florida.

 I'm still not sure if I want to move there fulltime, but I thought it would
 be neat to at least build up a customer base down there, perhaps enough
 to finance a long-weekend trip.

 Here is the plan I am "mapping out:"
 
 1. Do a "virtual reconnoiter" of the Ft-Myers/Naples area - 
    study maps, look at pictures, etc using online resources
 2. Talk to the Naples chamber of commerce about the business
    climate, etc.  "Tickle" them for a future in-person 
    appointment
 3. Fly down for a two or three day stay.  See the areas
    for myself.  Get a sense of the business climate and
    quality of life for myself.  Meet with the chamber - 
    "network" a little
 4. Come back, think about it.  Place ads in local papers
    for my services - I already have a 1-800 number with voicemail
 5. If a few people respond, then I'll schedule them for the weekend - 
    new clients that answer my current ads are pretty understanding
    when I say, "I'm booked up until the weekend."
 6. Fly down and take care of my FL appointments.  The twist: 
    give each PC extra TLC - scour more thoroughly for spyware,
    viruses and problems.  Do several "test reboots."  Leave
    the client with some self-help troubleshooting tips.
    I certainly don't need any "panic calls" from someone
    trying to get me from NY to FL!
 
  What I'm looking for from GA: someone who can point out flaws
  in my idea, or tell me if my thinking is absurd or on-target.
  Anyone who's run a business in two disparate locales
  would be welcomed in their wisdom.

  Thanks!

I would absolutely invest in obtaining professional reports containing
 current demographics of your target florida markets and details of
your competition. A disproportionate number of small businesses in
every industry struggle and fail in florida due to the strong
competition posed by local and national players in every industry.

Decidedly NOT a good idea.

A new business will need A LOT of your attention and what happens to
your old business when a crisis arises ... as it will.

You simply can't be in two places at once, can you?

A new business needs your full attention and you can't give full
attention to both places at the same time.  I believe your personal
presence is needed, especially so for a service business like this. 
If you were offering a unique product or service, you might have a bit
more latitude, but there are plenty of computer technicians in both NY
and FL who will be more than willing and able to step in a serve your
customers when you are not around.