First time purchasing a liveaboard

[barleyrye]

Hello
I am seeking the boating communities opinion on the best live aboard for my situation. A little about me, first time trying the live aboard lifestyle, and as such this will be the largest boat I have sailed. I am going to keep the boat in Charleston SC, for at least a year with the intention to move up north towards Annapolis, Baltimore or Delaware area, after gaining some confidence.
What I’m looking for is a capable boat that I can sail up and down the coast on my off days, and once in a while make a crossing to the islands.

My parameters:
Single pilot setup, Ideally 3 cabin (main for me, guest cabin, and storage in 3rd), air conditioning, GPS/auto pilot, fridge or freezer, in a perfect world some division between bathroom and shower, ac inverter for some electrics when underway, nice cruising boat, not full race oriented, that being said I do love sailing so I don’t really want a dog when under sail either. Semi easy to launch for a afternoon sail,

Price: 50-85k

Below is a list of boats I have been checking out, let me know what you think, or if there is something out there you recommend besides what I have listed, by all means I am open for suggestions.

Boats interested in:

1989 catalina 420
Catalina 420
I had the chance to view this boat in person this weekend, and was really impressed with the overall condition, I would have never considered going this old, but I was shocked to find this in way better shape than some 1995-2000 beneteau.

Concerns: Older boat, some outdated electronics, time on diesel 2600hrs

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1995 beneteau first 42s7
1995 Beneteau First 42s7 sailboat for sale in Connecticut

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2005 beneteau Cyclades
2005 Beneteau Cyclades 44 3 | eBay

Concerns, need ac upgrade $$$$, no hobs meter on diesel, was run as a charter for 5 years, out of the country complications

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Catalina 36 mkII
Used 2001 Catalina 36 Mkii, Lake Texoma, Tx - 76245 - BoatTrader.com

Concerns: Could be on the small end,

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1991 Beneteau 4 5f5
1991 Beneteau 4 5f5 Sail Boat For Sale - www.yachtworld.com

Concerns: Unable to reach owner, has not been sailed for almost a year,

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1994 Beneteau Oceanis 440
44' Beneteau 440

I had a chance to see this boat, overall condition was ok, seems like there is less space than some Catalina 36 mkII,

Any help, or input would be greatly appreciated!!!
THANKS

[Hudson Force]

Originally Posted by barleyrye

.....................
............................ I'm going to keep the boat in Charleston SC, for at least a year with the intention to move up north towards Annapolis, Baltimore or Delaware area, after gaining some confidence.
What I’m looking for is a capable boat that I can sail up and down the coast on my off days, and once in a while make a crossing to the islands. ..........
.........................

I would find it difficult to evaluate and share many opinions about a boat online. It might be best to shorten your list by finding those that meet some basic criteria and rely on a survey for a potential buy.

I would like to share some thoughts about the year in Charleston to gain experience. Any protected water for gaining experience and learning is limited to Charleston Harbor and the currents can be fierce. Sailing "up and down the coast" or "crossing to the islands" is a far more challenging task than the many easy destinations, anchorages and milder current cruising in the Chesapeake. I would strongly advise that you take your early time gaining experience in the Chesapeake where you will also find a larger used boat market.

Oh... and Barleyrye, Welcome to the community!

[barleyrye]

Thank you very much for your input. I agree a survey is a must, and I already have one for the catalina 42. To be honest I assumed Charleston would be a good learning environment, already knowing the area, and having a few friends there. But I will definitely take your suggestion into consideration, and look at learning up north first.