As many have pointed out, the trick is matching your values, desires, skills and approach to the right strategy.
- Do you enjoy planning and devising a travel plan?
Personally, that is half my fun so I don't have big issues about being able to book time when and where I want because I'm ready to book early on. We have friends that hate that and ask me to help out. We don't own any fixed weeks (which is it's own unique conversation). I like having hundreds of places to go to (without exchanging) by being in a variety of systems. If you don't like the planning, hotels and AirBnB are much more flexible.
- Is it super important to you to get the absolute best deal?
If so, then dollars and cents may be a primary driver for you and you will focus on bargains to be found in hotels or AirBnB. We have bought lots of resale and some developer. Our most expensive purchase is HGVC W 57th St in New York City. From a dollars and cents perspective I'm pretty sure it wasn't the cheapest way to go, however I don't regret it. We love feeling like we are coming back to our home. We love the staff and the location and the whole experience of staying there.
- What does travel mean to you and what is it likely to mean in the future? (For example, a lot of our travel was around skiing but we can't do that any more.)
Travel has been our favorite recreation for the 40 years my husband and I have been together - not just since retirement. Even if we just hang out and don't do a lot of "activities" in our travel location (which is happening more now as my husband is slowing down) we love being there and experiencing other views, other weather, other sights on the drive and other physical condos. Obviously, if you aren't into a lot of travel, there is no need for a lot of timeshare ownership.
- Are you a go go go person that is mostly out doing things or do you like to hang out on a deck and enjoy the view and cook melas in?
The more you lean to the later the better fit a room timeshare will be vs a hotel room.
- Do you have children or others that understand and would make use of your timeshares once you no longer can.
For us, that's a big question mark as we don't have any kids or obvious recipients. However, we based our decisions on that knowledge. If there are people in your world that would want your timeshare then you can plan on longer value for them.
- Is travel variety important to you or would you be happy spending most of your time at the same place.
Variety favors timeshares. Lot of time in the same place - maybe buy a vacation home and get appreciation.
Lastly, a bit about us and why lots of timeshare works for us.
We own a TON of stuff and spend 6 to 8 months of the year on the road - mostly in timeshares. Our Maintenance Fees for all of our ownership runs about $1000 per month which we can afford.
The average person would probably not want to own that much but it works for us.
Every place we come is spic and span clean. When we leave, we take out the trash, run the dishwasher and let somebody else make it spic and span for the next person.
Most places we stay have kitchens and washers and dryers making food costs and laundry cost similar to staying at home.
We get to enjoy beautiful mountains with gorgeous weather while it's 100 degrees at home.
It's easy to return to the resorts in our systems that we really love and we know exactly what we are getting.
If you have flexibility, you can really stretch your timeshare $$. A few examples:
- Caught a low season Monday (week days are cheaper) at WM Running Y last December and only paid $35 for a one bedroom condo for the night using FAX time which has no minimum nightly charge.
- Just spent 6 days in Sun Valley in a beautifully redone two bedroom two bath condo looking over a golf course on the last days before summer season (the week before the 3rd Friday in June) and paid a total of $312.02 in MF and booking fee - that' s $52 per night because off season points required were low.
- We spend several weeks each spring and fall in a beautiful two bedroom cabin on the Sun River. They are cheap due to a quirk in their point system (probably before the units were as nice as they are now). There are only 3 of these cabins so it's tricky to get them booked. MF and booking fee for a two week stay is $542 or $39 per night.
- I book week days in timeshares and use weekends for travel/hotels as weekdays are much cheaper. In a number of systems, Monday to Wednesday nights cost half as much as Friday or Saturday.
- We love WM Park City. It is across the street from the Waldorf Astoria where similar accommodations would run $1500 - $3000 per night during February when we usually go. My gorgeous two bedroom, three bath, two fireplace unit costs me about $1000 in MF for the week. It's true that a maid will come in daily at the Waldorf and they will transport my skis to the bottom of the lift but I'm not sure it's worth the difference in cost.
So, whatever you decide, make sure it fits and enjoy your travels.