Keep the one you have, just sell the big tow truck, wife, kid/s

will save you years of grief

I would suggest talking a bit more with your wife. Discuss raising the mast, standing in the water sometimes waist deep holding the boat while you get your truck, child crying etc. The trailer sailer would soon end up with all those other trailer sailers with grass growing up through the trailer. Buy a bigger fixed keeler.

One factor not mentioned by Knight in the intro is that he has a job which moves him around the country. Hence the advantage of a trailer/sailer is that it can easily follow him and the family wherever he is posted.

Sorry, I am not a fan of the Compass Careel Mks 1 and 2 if you have no tow weight restriction, as they are not properly self-righting.

A bigger version of the Investigator 563 concept is the Sunmaid 20. The Boomerang 20 is another stable T/S but the drop keel is an issue in the cabin. Ultimate 18 is similar.
More info on the Investigator at investigator563.com/Forum/

Chris 249 said..
How much of an issue is self righting in small TYs? The only times I've been in a CC 18 I've been struck by how practical they were as a family boat. I did see one capsize, but that was about 40 years ago and given their popularity it doesn't appear to be a high risk. Any small boat getting knocked down to that sort of angle is a health risk to a "family crew" anyway.

There's upsides and downsides to all small boats. I knew the Roses of Careel fame, and they said that they felt the CC18 was very good for kids because the lack of a keel meant they could take it right into shallow water where the kids were at less risk of falling overboard when young. Obviously they were biased to their boat, but it was an interesting remark that showed the factors that had to be balanced.

Knight, what sort of a sailor are you? Do you like overnighting? Do you like to tweak, or like to set and forget? What sort of launching ramp do you have? Do you want to take the boat right into a beach, or anchor out?

Getting to the beach is not a problem with the Investigator 563

Not a real TS fan but Ive always liked the look of the Masrm 720

dreamliner said..
Not a real TS fan but Ive always liked the look of the Masrm 720

absolutely love them Merv built a great boat his workmanship and eye for a fair line was great but maybe a bit lively for a young family and is well over the 20 foot and i doubt you would get one in reasonable condition for that price

Since so many people here are so disparaging of TSers I suggest you are in the wrong T_ _ _ _ _ _sailerplace. a bit more looking and you'll find a whole bunch of people who know how to TS.

This came up not so long ago either. A thread search may help.

As for my 2c, I love ts'ing. If mast raising is so hard you're doing it wrong. I have zero knowledge of the size you're interested in so I'll move along.

I down sized for a trailable trimaran after I sold my H28, sold it 3 months latter and bought a 38 footer. it was a good idea on paper but it didn't work out for me.

We had a Princess 18 for a while when we were at a similar family stage. Spent a few nights on it with the kids. It would never win races but sailed well enough to be enjoyable and was incredibly roomy for it's length with a raised foredeck and twin daggerboards. I sold it for an Endeavour 26 (which I have since sold) but often wish I had kept the Princess. We may not have used it more frequently, but were able to easily use it in more places. We are at Lake Macquarie so just an hour or two to Myall Lakes, Port Stephens, Hawkesbury, Sydney Harbour and Port Hacking plus some visits to inland dams.

No real difference in set up time in my experience. Load up the TS at home in the drive way and drop it in the water at the ramp. We were on the water in the same time it would take to row out to the mooring. I could raise the mast myself by hand easily enough on the Princess - even out on the water while we were motoring away from the ramp.

Spent 3 days at Port Stephens with each of those boats in similar conditions. Found the TS much better with little kids to be pulled up on the shore rather than rowing backwards and forwards. On the flip side - enjoyed the headroom of the Endeavour.

Pros and cons.

All the best,
Richard.

Wow, I didn't expect this level if response, thanks for everyone's thoughts.

A few answers to questions and clarification.
As Yarra said, my job moves me around the country on a semi-regular basis, and at the moment I'm in Sydney and the yacht is still in Newcastle. I'm on the list for a mooring down here, though how long that will take is anyone's guess. So yes, having the ability to take the boat with me when I move is definitely a part of the decision.

[Quote]Knight, what sort of a sailor are you? Do you like overnighting? Do you like to tweak, or like to set and forget? What sort of launching ramp do you have? Do you want to take the boat right into a beach, or anchor out?[/Quote]
I've been around boats on and off for quite a while, but normally I've been crewing on races, my Top hat is the first boat I've owned and regularly used. And I've definitely learnt a lot by doing more than races.

I do enjoy overnighting and loved the couple of weekends I spent moving the yacht up north originally. However, I am time poor, mostly as a result of family commitments, and Sailing away for a few days on the yacht up and down the coast just isn't possible at the moment. (When the children are of a suitable age however, I would love to take 12 months off work, put them in school of the internet and sail them around the country for a year - but that is definitely a future plan, and will need a larger yacht for that anyway)

I don't have a specific beach/launching ramp in mind. My wife however definitely does like the idea of pulling the boat in close to the beach, rather than a row out to a mooring (she isn't a fan of the inflatable dinghy we have)

I enjoy tinkering in electronics, however as can be seen from my previous posts both here and elsewhere about maintenance, I'm fairly hesitate and very much only starting to learn how to do the hardware tinkering, though the skills I have learnt have been good and very much enjoying learning.

I recognise that everything is a compromise and that everything has a cost (in time or otherwise) as well as a benefit.
Do I think a TS will be the yacht I own for the long term? No, I think I will want to do more than I can with a TS in the future, but I have to recognise that I (and more so my family) are not in the right place for that sort of Sailing at the moment. I have to be realistic with what is achievable at the moment. I did consider going all the way down to a large dinghy, but I don't want to lose the ability to have holidays on mostly enclosed areas, where as a dinghy really limits me to just a couple of hours on the water.

Thanks for everyone's thoughts, it's been good to see other opinions