Hi Tom,
Welcome to the forum, and I like your name
Ready hit the nail squarely on the head!
My advice is to take your time. Think carefully about how you will use the boat. For example: guests often or almost never; short duration trips or months at a time; protected waters or open water crossings, etc.
From there, write down (critical IMHO) 3 lists (wife and you write separate lists is best) based on how you plan to use the boat. Lists: Must haves; Nice to have; Do not want. For example, for myself, my do not want list included: screwed down teak decks (will eventually leak if not already and very expensive or time consuming repair); exterior woodwork (don't want the extra maintenance); twin engines (I do most of my own maintenance, and with twins in smaller boats, ER space can be really cramped), etc.
Then compare the lists, talk it out, and compromise. You probably will not find the "perfect" boat, and will have to accept some things not being exactly what you want.
If you are really inexperienced with boats and boating, then go to boat shows, take some courses, talk to other boaters, walk the docks and ask questions, etc. to help you understand boat features, and what ones might be important to you! Past maintenance is also critical, especially in "older" boats. Written maintenance records would be a definite plus.
In my opinion, short cutting this process, especially if you have not owned similar boats before, could easily lead to you making a mistake in your initial boat selection resulting in either a resale, or putting up with a boat that does not really meet your needs as well as it could. Both, in a way, costly.
Enjoy the process, and it is a process,
Regards,
Tom