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Thanks for the reply Ken. My original plan was to continue to save and search for the right boat over the next year / year and a half, then hopefully move aboard full time, year round. However for this particular boat, since it popped up out of nowhere, I would purchase immediately, and keep on the hard for as long as needed until being able to move onto it. I am thinking that realistically that wouldn't be until Spring of 2019. I have about $26,000 total in "Boat Fund" right now but that should be closer to $30,000 by the end of the year, so the Idea would be that after purchase I would have about $8,000 to put towards storage, fees, maintenance and improvements over then next year and a half and towards making it liveaboardable. If it ended up being significantly more than that, I would have to dig into my safety net / savings, which I really don't want to do. However, once I am able to move aboard, I will have roughly $12,000 a year going into my boat fund in perpetuity, which will need to pay for all maintenance, repair, improvements and slip / storage fees etc. Basically anything boat related. Let me know if this didn't answer your question, and if you think this is a realistic plan.

EDIT: Forgot to mention that I am in New England, and looking to eventually live aboard year round.

I absolutely love the layout of the Catalina 34. Staying on one a few years ago really made me fall for the model. Everything just felt right on that boat, and I especially loved the aft head and cabin situation. It just feels like the perfect setup. I've been saving for the last year for a sailboat that I plan to both sail and live-aboard, but unfortunately my budget for a purchase (while keeping enough leftover for maintenance, storage, dockage etc) is $20,000 or under. Because of this I am definitely priced out of Catalina 34s.

I had all but settled on a Pearson 323 because they sail great, they're made well, and aside from feeling a bit more cramped than a Cat 34,  I really like the layout.

However, recently a Catalina 34 has come up locally that was donated to a church to sell. They are asking $19,000 for it.  The only thing that I know about it is that it has an original motor (m25xp with 1,333 hours) and it was sailed frequently until 2015. It's been on the hard winterized under shrink wrap for the last 2 years, however the engine is always run for "at least 8 hours non stop once a year" then re winterized according to the disclosure from the precious owner . It has original Sails, which have been repaired many times, and I am told "all systems working 100%".

I was able to visit the boat a few days ago to get a look.

Here is a link to the Album https://photos.app.goo.gl/eC8uzUmS3ys7PD9k1

There was a lot that looked great about the boat, and a lot that didn't. My photos are mainly on what didn't look good.  All the wiring looked like it had been refreshed recently and installed well, and all living areas were well kept and well taken care of. The deck was also in very good condition (besides the chain plate and stanchion repairs).  I am trying to get an assessment of how this one compares to the other boats  on this amazing board, and get an idea as to what might be in store for me if I end up purchasing it, and whether or not this seems like a good buy.

The chain plates all seem to be leaking, there is what looks like some pretty serious keel weeping with the catalina smile, and the bilge looks terrible and rusty (although the bolts don't look that bad). There are two places of significant rot on the interior wood paneling, shown in the pictures to the right corner and left corner of the VHF unit, and one single spot on the starboard size, but not anywhere else on the entire boat. Every other inch of the boat's interior wood seems strong and dry, with no signs of damage.

Many of the stanchions look like they were poorly rebed but there is no crazing around them and they are all very firm. I did not feel any soft spots on the deck. The Entire rest of the boat seems fairly solid. The standing and running rigging look good and all of the winches move very very well (As do the seacocks). I'm a somewhat talented shade tree mechanic (do my own timing belts, suspension, brakes etc) and am also fairly talented at most anything DIY, so I'm not worried about labor intensive projects that I can do on my own, but I do want to know how bad this one looks compared to what you all have. It seems like this is a good deal even with new sails, chainplate replacement, and keel resetting factored in, but if the chainplates are so bad that the deck needs a recore, that would be way out of my comfort zone. Even though the motor supposedly runs very well, it looks terrible. The oil pan almost looks like it's rotting away and there is oil and belt spray all over the rest of the engine. The oil looked fine, but it was recently replaced. Any input that you folks could give me on how this 34 looks, and how the price of 19 compared to what she's likely to need in the near term. Am I just getting my hopes up because I love Cat 34s so much and I'm desperate to make this one work, or is this a potential diamond in the rough? Should I be interested in this one?

I've spent many many hours researching on this message board, and have read all of the stickied information, including the buying guide written by the gentlemen selling his amazing 86 CAT 34 for $39K a few years back. It's just hard to compare the one I am looking at to his, since his IS BEAUTIFUL.

Thank you all so much for your time.

Ryan