When it comes to boats, Everyone has a different plan ! some times plans don't work out. So the plan can differ from what reality turns out to be.
So sometimes, the plan & what you actually do with your boat, can be two completely different things. So think twice or three times before you jump.
I see your in So-Cal, - Orange County area. So your probably planning on keeping your boat maybe in Dana Point Harbor, Newport Beach Harbor, H.B. Harbor or Long Beach Harbor, or maybe even San Diego Bay ? -
Have you priced out the slips at these harbors ?
Do you know their insurance requirements ?
Do you know the slip availability where you want to be ?
Things to consider, like, is there a waiting list for your size slip ?
Do you know what the marina's insurance coverage requirements are ?
Do you know what the "must have insurance" will cost you to have, as you can't get a slip with out proper insurance that meets their requirements
Also often to get that insurance you need to have a good & current vessel survey to get that insurance. So vessel must be up to specs.
For us to give you some realistic & useful info, We need to know some basic information on how your going to predominately use this boat ?
How many expected onboard as guest ?
Will you be single-handing ?
Will your trips be predominately day trips ? --
You said costal cruiser ? & you mentioned Fly Bridge preferred ?
or will a lot of overnight trips be the norm ? & therefor how many a boat will comfortably sleep is a key thing to look at ?
What type of engine - Gas or Diesel is preferred by you ?
Don't forget to consider how many Heads (bathrooms) you want as well ?
Showers ? other creature comforts like maybe A/C or heaters ?
Water tank size wanted ?
Do you want her to be Water-maker equipped as a priority ?
How many will be crew ?, etc., - Maybe just one -- like you & the wife ?
or will it be four fishing buddies?
That means to consider do you want a center queen bed for you & the wife, or do you want all single births for you & your fishing buddies ?
Also Budget ? -- You said $ 200K or less. - does that mean Turn key at $ 200 K ? or what if the boat is $ 200 k & still needs $ 25 k more in fix up ?
Are you handy & want to do a lot yourself ?
Realistically do you have the time & constitution to do the fix up ? or do you want to be out on the water cruising, not fixing stuff all the time ?
What fuel Mileage you want ? - You mentioned single engine. (Big or little HP engine size ?)
What speed do you want ?
What range do you want ?
What navigation gear equipage do you want ? Radar ? VHF ? Depth ? GPS ? compass, etc. -- what vintage of that gear do you want ?
next shop around & see - Is what you want available on the market at your budget price, etc. What are you willing to compromise on ?
Boats are a compromise.
But I do understand you want something nice & you mentioned you were influenced by resale value.
A friend of mine has a Nordhavn Full Displacement Diesel Trawler & crossed the Atlantic & toured the Med & came back, but is now selling that & getting a Semi-Displacement Grand Banks with big twin engines to do the great loop & ICW, -- So Both are Great Boats -- But are different designs for different usage.
So as you see different boats are needed for different usage.
Different boats meet different missions specific needs.
Here are some questions to ask yourself " what is my mission on my boat ? -- & - And sleep on it & talk to the Admiral about it first, before you decide. Then we can guide you.
Is this for live-aboard & not regularly leave the bay ?
Might you be planning on crossing oceans or at least want that option ?
Are you planning on going far afield from home like to the Panama Canal or Alaska ?
OR - are you just going to stay predominately local & to go to Catalina Island on weekends & maybe the Channel Islands National Parks five-islands on your two weeks vacation every year ?
Or are you staying in San Diego Bay or Newport Bay, or what ever & only venture forth for a few hours in perfect weather days in the open ocean ?
Or are you going to do the Great Loop up/down the Mississippi River & Great Lakes & ICW or similar stuff like Petaluma River up in the SF Bay & upper bay & Delta Area?
Or are you looking for one that will be your weekend condo on the water ?
All these questions are addressing possible things to consider & are all legitimate uses of your future boat, but different boats are better for different missions & different budgets.
Looking forward to your answers & I am sure a lot of TF guys will help you out.
BTW - There are some old threads here you can search for, right here on TF, as many before you have asked the same questions & this would allow you gather some basics in info of what to think about before you respond - look those over too, all are here on TF for you to peruse. Here are a couple boat brands I have cruised on that might fit your needs - Just a couple of many options out there to consider, so just throwing a couple names out there for consideration.
IMHO - Grand Banks 36 is a possible contender in single engine boats for So-Cal Waters to consider or other similar makes of that size. Monk 36 is another one.
IMHO - If you want more of an ocean going style, then the Kadey-Krogen 42 is a very nice Full Displacement Diesel Trawler, if your planning on going further afield. That is what my personal boat at this time is & we like it. -- But it is only a 7 to 8 knot boat, so not fast enough for some.
IMHO - For a twin engine the Grand banks 42 is a good choice & is a bit faster, but of course, depending on engine size & HP.
BUT remember for any used boat - The key is : Condition, Condition, Condition !