Crowe,
Life's desires usually change with age, jobs, kids, new ventures wanted, or family economic changes, or changes in the area/region lived in, etc. Some refer to the life's desires as "phases". Have to do what makes you happy or allows you to enjoy the phase you're in. We were very fortunate as we had both vacation accomodation structures and RV's to enjoy and add in the cabined powerboats and sailboats and it gave us so many choices.
Our home along Lake Michigan in West Michigan, a winter vacation home in Florida and one in Northern Michigan that we planned on just driving a vehicle to or flying to the one in Florida. Got to hate flying as we both had done it so much and it didn't happen because we drove one of the RV's, usually the truck camper, with our trail motorcycles or snowmobiles or boat on a trailer behind. So we bought a boat to keep at each location and had a storage garage built to keep the boat and either the trailbikes or the snowmobiles per the season in so we didn't have to haul them. However, we'd still take the truck camper so we could do overnight or a few days adventure/explorations so we really gained NOTHING.
The kids grew up with this type of life and loved it but then, of course, got married and out popped their kids so they we very busy working etc and we'd take the Gkids up north with us sometimes so they could experience what their parent had and they loved it too. However, the constant work of keeping up the places everytime we went to them was all on our aging shoulders then and my wife had serious back and neck issues. Guess who was left to do the work almost from the time we arrived till we went back home? Add in the property taxes and insurance on 3 lotacions and the maintenance cost of weekly yard work in the Florida place as the grass and weeds grow like crazy in the spring, summer, and fall down there.
Very expensive and for what? Using it in part of the winter as nobody in their right mind would want to be in the extreme heat and humidity in the hot months! Mold and bugs was always a problem too so bi-monthly spraying was required and being unoccupied, the insurance rates skyrocketed as has everything else in Florida. The sun, mold, and heat took it's toll on the Florida boat and took it back north to totally refurbish and sell and sold the property in 2007 and just in time before the real estate/home/condo market values dropped more than in half. Whew, dodged a huge bullet!
Still have 2 of the 4 places we had in Northern Michigan but seldom go to them as is simply RV'ing for us now to both Florida, Northern Michigan, the U.P., Canada, Alaska again, and you name it. The condo's and vacation homes don't move to anywhere different as they are on foundations and taxed and require insurance and maintenance etc whether we even go to them or not.
Crowe, we basically did just the opposite in sequence of what you are talking about. Worked for us but never would have if we'd reversed the sequense! It will amaze you how much it really costs per year to have a cabin/vacation home in real dollars. You are in an area that gets really cold and water lines freeze and break among so many other liquid things such as canned goods etc. So take all liquids home and drian/blowout the lines after every stay or leave the place heated and that's sure not cheap. Maintain the yard and clear snow? How about security and it being broken into when not there and ransacked or the good things inside stolen? TV, Range, microwave, small appliances, you name it and they now have it! You may find some of your stuff at a pawn shop and never know who bought their drugs with your help! Don't forget about septic system repairs/pumping or other utility costs. Taxes and insurance plus property regulations are only going to increase in the future as is maintenance costs.
Not trying to convince you one way or the other as that's your decision alone. Just pointing out some things to consider.
If you don't care to pull or drive an RV simply putting an appropriate RV on a seasonal site of your choice or at a different location each year so you can enjoy a variety of experiences eliminates most of the security and fixed cabin/home/getaway issues and you'll pay the known seasonal costs only once. Then you can drive any vehicle to where it is day or night and not have to fight traffic with an RV rig. Once you pay the seasonal or yearly cost, you have the right to leave with your RV anytime or at the end of your paid period and it's blessing if you don't like your neighbors or what's happening in the area that affects the resale value or tax bonds passed. Controlled costs and cheap insurance with an RV and no fixed home issues and no lingering surprises. RV's lose value with age with is a fraction of the investment of a non-motorized RV. Real estate on the other hand is a very large investment with high ownership ongoing costs but can increase in value or decrease in value and you have so very little to to with which will be the outcome!
Wishing you "good luck" with whatever choices you make!!!
