I want to know how you guys make the go for it vs. doing other things so I can improve my fun time vs. wasted time vs. misses...

Here is a long (very long) description of how I make my tradeoffs.

I put this under the buggy section instead of under general because when I used to windsurf in the Hood River Gorge area we had a pagers (long before cell phones - lol) system with wind speeds, sun levels, pressure and air/water temperature readings along the river etc.
You went to the first good spot out of the rain and into the sun with the right pressure setup and you would get wind 90% of the time...

I am going to ignore the obvious buggy question of tides / rain etc.

You guys are going to think I am crazy because I only have to drive 5 miles from my office (in 6 minutes) or 19 miles from home (in 30 minutes during normally traffic) but here is all the stuff that I do...

I look at windfinder.com - and I always use 2 sites - the local air port and South Beach State Park
I mentally correct the readings for the wind direction etc.
So for example - the sensor location at South Beach State Park is back from the sand and has a dune just to the S of the measurement system and a rock wall jetty wall < 50' to the N of the location. The sensor is not very high in the air so these details have a large impact on the readings.
The air port sensor is about 3000' off the beach on the other side of the express way which can often screw up the readings a lot including even the direction at times. The good part about the air port is the measurements are constantly updated 1 time per minute on some web sites.
There are maybe an additional 5 sites around but I find them fairly useless which is amazing and frustrating to me.
I find looking at the off shore buoy reports is also not very useful.

If at my office and I am on the fence - I walk out to the express way (< 100 feet) which runs N/S (parallel to the wind dirctions on the beach) and look at one business' advertising flag.
I also have 3 sets of trees I look at really closely.
In better winds I just go for it.
In nuking winds - I hear the building shudder - when my dog hears this he wants me to know about it so we can get moving NOW but he has trouble understanding tides - lol

At my house - it is easier in some ways but harder because I have to drive farther and take more of a gamble on the wind vs. time burned equation.
I normally just look at how the grass moving (which is 40' above the ocean on a rocky bluff) and the wind meter sensors for direction and speed on 3 local houses (you would think I would put up my own sensor LOL) - I watch to see if the buildings are swirling the wind and if the sensors are moving at a consistent speed.
I will also look at the winds moving the trees up the hill toward the expressway - this gives me a cross section of the wind up 500+ feet in the air to look at.
And I listen to how loud the express way is if I can hear it at all. This also must be correct for wet vs. dry road.
In higher winds it is trivial of course - I see the wind patterns on the ocean.
In nuking winds - I see the large view windows bowing in and out. (I just replaced them so I am getting still getting re-calibrated :o )

In the summer - my local info gets shut down at times.
We can get a lot of fog (blowing cold - dense fog) when the central valley in Oregon gets hot - the water is 52 - if the valley is over 90 - we often get the blowing fog and a West wind coming off the water.
This condition will almost never exist at my buggy site - the fog actually is often gone 2000' to the S of me on the other side of a hill.

When I get to my buggy site - I look at:
The blowing grasses.
The blowing sand but this often changes with days from wind direction change, time from high tide, swing of tides, time from rain, wind direction etc.
I really like to walk toward the ocean, gauge the size of the surf and see how loud the surf is how far away. This often tells me more about the wind and which kite to use than anything else.
The modulation of sound level with distance is also a really good indicator of gusts and the minimum fill.
If the wind is marginal and dropping I find listening to the sound of the express way traffic away from the beach to be useful to see when I must up the sail size or call it a day.

I suspect everyone has a set tips and tricks we use to get better wind info to have a higher fun ratio.
I feel like I get it right about 75% of the time - so I want a higher ratio...

So what tools/techniques/tricks do you find useful?

I kind of think that you're batting with a pretty good average as it is.

I don't care to overthink it too much. If my WindAlert app gives me a decent reading on the wind and tides I'll give it a shot. Worse case scenario is if you get there and can't ride, oh well, plenty of worse places to be than relaxing on the beach.

Curious about where you preferred riding spot is. I likely ride the Newport beaches more frequently than anyone else on this forum(though I guess now that would depend on how often you do:D) ... At my go to spot down there high tides don't even stop me.

Also, I find the S. Beach weather station to be relatively trustworthy as long as it is not a S-SW wind.

the biggest thing that matters is direction. everything else is down to your quiver.
for your initial choice of kite buy yourself a wind metre then if it picks up and you get overpowered get a smaller kite out.

MeatDriver interesting - tides have a huge effect on all my riding spots???

I think I have kind of a different style than is typical.
From my windsurfing days - if it was below 18 mph my boards were all small enough that they would not plane and swimming was not much fun so I got used to playing in a lot of wind.
I still like high winds with fast turns - so if the wind readings are below 15 mph I probably will not bother because 1) I do not have the kites for it - even my 7 meter kite to me is massive and feels slow to turn and 2) the buggy I use is a Flexifoil Navaro so not exactly a cruising machine.

The N/S winds and high bluffs around here for me created an across the beach ridding style of short in and out runs toward the ocean.

I think I have only gotten 3 days with a W wind where you could go miles down the beach.

My first selection is to go to Ona Beach - 90% of the time on the N side of the river.
Sometimes the river shifts so far N that I go for the S side but the bluff can make a large wind shadow.

I also but rarely go down to Waldport on S side of the bay inlet - it can collect a lot of dead wood at times and the sand is often very soft around the corner of the bay inlet.

The N side of the Newport Bay inlet looks promising on some E wind mornings when the winds flow out of the channel but I have not got that together yet. Tried a few times but no go.

I have also eyed the bay to the south of Lincoln city - it dries up pretty hard during some low tides and the S winds can be good if you stay away from the houses on the S side and W outer ring.

I have also considered S from South Beach State park - past where most of the people would normally go for a W wind day.

For me it goes like this... I will pick a Saturday where I know my family either doesn't have group plans or where my kids are out with my inlaws (typically making plans a week ahead). I ask/tell wifey I'm thinking of kiting on that day and then I watch the forecast like a hawk, usually checking 3-4 times a day. If the forecast on said day (day of) is below 9mph, I stay home and petition for another day. If 9+ mph is in the forecast, that usually means at least 6,7-10 mph winds which I will fight with my 8.6m and "make it work".

I have 4 kids 9 yrs old and under, so I lack the luxury of spontaneity. I am lucky if all the stars line up for an awesome session as I have personally limited myself to one session a month for the sake of being there for my family. I also strive then to make that time count for however long it is. In essence my sessions consist of shooting for a day and then praying.

I live WAY inland so tides don't factor it... But I am ALWAYS watching the trees and flags around. I have noticed that all of the deciduous trees in my area have a much lighter underside of their leave, almost white,... So if it's blowing really hard, I will say to myself that "the trees are white-capping". It's just what I look for to know its a good wind.

I do occasionally (2-3 times a month) grab a static session on my lunch breaks, but that mostly consists of watching the forecast and comparing it with what I see outside. ... 9-10+mph = kite lunch.

That patch that forms as the tide is receding in south Lincoln City has treated me fairly well. For sure the best spot in LC with the prevalent NW wind. Though once your moving at about 25+ the ripples in the sand will rattle your fillings out.

As far as the north inlet area in Newport with an east wind....terrible access. Sean aka CSADeadon told me of Ona and is a solid place to buggy at low tide.

Unfortunately my "sweet spot" where the tide isn't a factor, most often requires BF tires. Agate Beach is my favorite playground especially with hundreds of rolling dunes that appear in late spring and stay until, well....last week. The recent storms have washed the dunes out with high surf and wind. I imagine by now it's relatively flattened with a decent pack. May be worth a stop by the parking area to check its condition. Wednesday would have held some fairly speedy runs even with barrow tires, but the rain was keeping me out.

My best bit of advice would be to make it to the SOBB events next year. Was just out on that beach yesterday with a 15-20 SW.... could have spent all night there. You'd be hard pressed to beat that beach, which has a nice drivable hard pack year round.

MeatDriver on the Agate Beach location - Do you start at the pull off across the road from the Best Western and then head N?
Is parking a problem - I think there are about 8 spots there unless you park in the large paved lot to the E of the road?
I always assumed Yaquina Head would screw up the winds - what wind directions work best?

If you ever go S from Newport then you might check out Driftwood Beach before you get to Waldport - it gets the same dunes as Agate but bigger from the few times I been there. Just ignore the on-line wind readings out of Waldport as they are completely misleading.

Have you ever checked out the Bob Straub state between Neskowin and Pacific City - it looks on a map like the winds from the west could flow inward over the beach without much restriction toward the S end and I would expect very few people to be present - access to that area might be better going down the beach from Pacific street on the N of the park?

How big is your driving route or is this un-related to your meat delivery area?

I forgot to add that I also watch the birds - Sea Gulls, Vultures, and Eagles are the most useful because they are big enough to really work at using the wind currents and big enough to see what they are doing.
Pelicans are common and big but not very helpful because they hug the waves too much in most winds.
Nothing is quite like seeing a Vulture hanging around above you - you can just imagine it thinking - hum this one looks out of control and with a really good crash I will score.