We're taking a little bit different of a tactic than are you - mainly just a longer timeline. We're also in DC - our timeline is to leave in 4 years rather than 4 months
What you've outlined is certainly not insensible, although there a few things I would do right now if I were you:
1. Start looking at actual, available boats *in person* right now. The reality is always very different than the pictures, and you've got to look at real life boats in person before you can start to really "read" a picture and "see" what it's telling you (beyond "oooh, that looks nice").
There's a very good chance that once you view half a dozen boats in person that your expectations will shift some (most likely there will be some "we'll need a bigger boat and/or budget than we were thinking).
2. Take pictures *AND* lots of notes as you view boats in person.
3. Start developing a checklist of things to specifically look at. There are a few books
and articles on questions to ask yourself/checklists to go through as you look at a boat - read them, and tailor the questions to your specific situation/preferences (especially around the "work from home/boat" aspect which until very recently have been unaddressed in the classic
"checklists for looking at boats" - e.g. do you need two work
spaces? will you have to both be on conference calls at the same time? can one person use the galley/head/any boat system at all while the other one is on a business call, or will they have to quietly do _____).
4. Once you've done the above, start casting a very wide net in looking at boats for sale
. If you find a make/model/year that checks all your boxes but that particular one is too expensive or needs too much work, write the make/model down so that you can look closely at any others when they pop up on your searches - this goes the other way too: if you eliminate a model because it just won't work due to _____, write it down so that you don't waste time looking at ads for that make/model anymore. We had 40 different specific make/models on our "we'd buy the right one of ____" by the time we made our purchase
(and a much, much longer "nope, those will never work for us" list - note: our "won't work" list had many very popular (and very good) cruising models - they just didn't fit what would work for us
5. Also remember that asking prices are just that, asking. Most are *very* negotiable (we paid almost 30% less than asking when we bought, and that's not unusual).
6. One thing that can be helpful is to post a link and pictures to any specific boat you're thinking about here - lots of people will point out strengths and weaknesses of the design and comment on specific things (good and bad) that they see in the pictures.
Lastly, I have no relation at all to this boat, and have only seen the ad here on CF, but if I were looking for a cruising boat in the DC area right now, I'd take an afternoon and go a look at this one:
If it weren't for the little pandemic thing going on, I'd be glad to meet you for a beer
, and discussion, etc - I also spent a lot of time racing
lasers (mostly in college) before "graduating" to bigger boats as a so-called "adult."