How old is your son? There is nothing like being young and have your own yard etc. to play in vs. a condo where you have to keep quiet and not disturb others.

Before you make any moves, check the Home Owners Assoc fees/dues etc There is alot of information on this forum about some of the dangers (and good points) to look for.

I would move to the condo. I would just make sure there are children in the complex for my son. A playground depending on his age and a family friendly environment.

Maintaining a home alone is no fun, although I suspect with insurance at $5200 per year, you might have a hard time selling your home.

There's a lot to be said about the conveniences of living in a condo, and it sounds like you might be a good fit. Besides what was mentioned previously, keep in mind that storage is usually a premium, although air conditioned rental storage units for seasonal items are usually reasonably priced when factored in. If there is no covered parking, you'll need to factor in the wear & tear on your car, but you might be used to that because most cottages don't have covered parking.
Look for a place that has lots of open space, walking to parks or beaches, and nice facilities (pool with bathroom is nice). In my personal search, I've found that a lot of these gulf-front condos have crammed the property with no guest parking, green space to walk your dog or ride a bike, just not outdoors-friendly.
I also recommend a book I just picked up at the library, 'Condo Buying & Ownership Made Simple' by Kay Senay (also available online as an e-book from her website, and other good info there). It's easy to understand and covers a lot of the legal stuff you should know in advance. The big thing right now is checking the # of short sales & foreclosures, and the reserves that the condo is maintaining. Are they still funding? If you need to get a mortgage, the lender will want to know these things, too. Many lenders don't do condos!
Be sure to ask about recent assessments and find out if there are any upcoming. This is stuff like when was the roof replaced, when was the complex last painted, last paving, pool last resurfaced, etc, and find out if those big-ticket items were assessed to the owners or paid out of reserves. That will give you a hint of how well the association is managed.
Good luck!

Here is a link that might be useful: Kay's website

I suggest you stay in the home and shop around to lower your home insurance. Insurance in coastal FL has gone down in many cases over the past few years. The price difference from carrier to carrier can be very massive. I am assuming it is the wind coverage that is high for you - or is it the flood insurance? Regardless, here are some tips to reduce coverege: 1) increase your wind deductible to 5% or maybe 10% if you can. 2) as stated before, shop around. myflorida.gov(look for dept of insurance) has list of all FL carriers. If your wind insurance is high via your regular carrier(that provides standard HOA insurance) then see about splitting the wind out to Citizens. My carrier went very very high last year and I simply changed carriers are saved a ton over what the new rate would have been.

Check with agents that offer insurance through several different carriers. Also you can change your coverage to insure only the home and NO CONTENTS(can split this by wind, fire and flood policies if you have 3 different policies.). This can be risky, but it might reduce your insurance by a lot. This is something I have done for flood and wind coverage and I am willing to live with the risk of losing my furniture and clothing and such and replacing on my own in the event of a wind or flood loss, which in my case is highly unlikely, though anything is possible(the home is covered).

Here are other reasons to stay in the home
1) the condo fees are likely to increase and it is also very likely there will be a lump sum assessment that you will have to pay. This is due to the many FL foreclosures and many condo unit owners are not paying their monthly fees lately. In the end, the other condo owners are going to have to pay for all these folks that are not paying - either via a lump sum or increased monthly payments.

Also do some web searching about condo associations and squabbling amongst neihbors and also between unit owners and the board. Folks can get real picky and whiny and you can be stuck hearing much whining and folks might whine about your child playing too loud or leaving toys out,etc. You will miss the freedom and peace that you had in a home.
If you want your son to enjoy a pool, see about going to a local park that has one, or the Y or similar. Or get a pool in your current yard - doesn't have to be in-ground, unless rules forbid above ground pools. After a couple years, your son will outgrow the pool. Do you have a gulf beach on the island for him to swim - maybe walking distance from your current home?

If you want a pet in the future, this can be an issue at the condo.

Hurricane prep shouldn't be that huge for you. You can have DH do some general prep before he leaves. As you know, there are really only a few months each year when hurricanes hit - and you really have approx 8-9 months of peace where you don't have to worry about prep for a storm.

A few thoughts:

Be aware that if you move to a condo, you will be living VERY closely to people who may or may not be good neighbors. In many ways, it is like living in an apartment--you may want to check out the "apartment living" forum.

Also, be aware that many condo associations have very strict rules about what you can/cannot do regarding landscaping, gardening, decorating, pet ownership, etc. Your life may be much more regulated than you have been accustomed. Also be aware than HOA fees can be increased at any time.

Good luck in your decision making.

Some people love condo life. Some people hate it. Since none of us know you, it is impossible to tell what camp you fall in.

Personally, I like having my own space. I don't want to hear my neighbor's every move. I actually like gardening, wood working, home improvements etc. Condo life definitely isn't for me.

At the same time, my father moved into a condo and loves it. After 30 years of mowing the lawn, taking care of a pool, etc he is more than willing to pay a little extra to have that stuff done. He lives in a cold climate, and the condo pays for snow removal in winter. He even gets along with most of his neighbors. Since he doesn't have to do all the little upkeep items that come with home ownership, he has more free time to do the things he really enjoys.

Moving into a condo in this market takes some steps that one would normally not do.
Because of the economy, be suspicious of the HOA's financial health! Ask them for a balance ledger to prove that the HOA has the minumum reserves, and are collecting sufficient funds to keep things right. Look at the exterior... is the mulch fresh, is the landscaping fresh, are the exterior surfaces cleaned and maintained, trash being hauled off, is the roof near it's useful life. Also, talk to the neighbors. They are the best place to get the low down on any community.
You can bet that both old and new communities that have units w/o owners, (foreclosures, new construction), then the HOA is going to be on a budget. You just do not want to invest in a place where the Association is not able to reinvest back into the community in order to keep your property values as high as possible.
As far as your concerns of moving altogether... I say if your heart says it is time to move on, then that is the best time to move. Couple that with the fact that it is now the best time in over 20 years to be a Buyer.
Good luck.

You said you could probably get twice what you paid for the cottage. If this is true then why not put it to the test before uprooting your family and hoping the condo works out?

Why not try FSBO or a flat fee MLS listing service first? Pick a price you would be happy to get and put a sign up in the yard with a flyer box. You will be able to see how many nibbles you get BEFORE signing up with a real estate agent and paying a 6% commission.

Another option would be to rent a condo in the desired area for 6 months and rent out the cottage during the tourist season. At least you could write off some of the taxes and have a place to 'go home' to if things didn't work out. Plus, this would give you a chance to see how much you and your family like condo living.

A link that may be useful:

www.flatfeemlslisting.com/index.php?gclid=
CMq-7azMxpsCFRSfnAod8yoUAQ

Many condo residents are older people or single residents. If you can't find one that has many children living there, it would be absolutely unfair to your young son to move. "Playdates" with other children are also much more fun when one has their own yard (and swimming pool).

timaran made some very very good points.

I live in a single family home in a development with a HOA. Unlike most HOAs this one is OVERLY active and run by a power tripping @#!&@!. They (really it is a "she") is nitpicking us to death (everyone has to wash the exterior of their gutters -- not kidding) or we will get fined. And they (she) will. Of course her house is a disaster but that is ok apparently.

I will NEVER EVER EVER live anywhere with a HOA again. If I wanted the convenience of a condo, I'd actually rent, not own. Or look into an apartment.

The homeowner has no power against the HOA. When we moved in, the rules and the president of the HOA were different. Things changed for the worse. Majority rules and if you don't have enough people who care, nothing you can do.