While "gear is no substitute for skill", the right gear can help enhance and support your skills.  When it comes to driving, we all put our lives in our hands nearly every day.  And choosing the right automobile for you can make you more comfortable, more proficient, and able to respond in an emergency.  I take a lot of time weighing the advantages and disadvantages of everything I buy, from shoes to cars.  Here are some of the things I consider when looking for a new car or truck, that could help you make the best pick for your needs.

• Does the vehicle have sufficient power for your driving style?  While an underpowered vehicle may get better gas mileage, it will suffer when you need responsive power quickly, and can become frustrating when it lacks the power to climb hills at highway speeds or must downshift constantly.
• Is the vehicle available with both automatic and manual transmissions?  While automatic transmissions may be more convenient, I prefer manuals.  Manual transmissions are far less complex internally, tend to last longer and be more reliable, can often "still get you home" after catastrophic lubrication or gear failure, get better gas mileage, and allow the driver to choose the best gearing for their particular situation.  I find it a little sad that driving a "stick" is becoming a dying art, when the main advantage of an automatic is just that it's less technical to drive.
• Do the rear side windows roll all the way down?  There is a trend to have rear windows that only roll down half way.  This is partly do to the designed shape of the doors, which need to clear the wheel wells, but also as a "safety factor".  Just teach your kids not to jump out windows and find the kind that roll all the way down.
• Do the doors automatically unlock when you open locked doors using the inside handle?  This is a great safety feature, since in an emergency the doors will open even if you panic and forget to unlock them first.  People are often found in accidents that failed to remove their seat belts and were unable to extricate themselves from their vehicle.  If you can't remember to remove your seatbelt in a panic, you probably won't remember to unlock the doors either.  It could save your valuable seconds that could save your life.
• How many 12v "cigarette lighter" power sockets does the vehicle have, and where are they located?  It's not uncommon for people to have several accessories that need power, such as cell phone charges, satellite radios, GPSs, power inverters, etc.  Some vehicles have power sockets located conveniently in the glove compartment, center console, or rear cargo area.  Some vehicles also provide some sockets that are always on, and some that are only on with the ignition, which can be convenient if you have accessories that you only want to turn on with the vehicle (e.g. satellite radio receiver).
• Does the vehicle come with in-dash navigation (GPS) system?  The advantages are that it is less susceptible to theft, generally "just works", will probably be integrated with the radio and other in-car electronics, and will be covered by the vehicle's warranty.  The disadvantages are that such technology is severely marked up by vehicle dealers/manufacturers, is often already obsolete, will quickly become excessively more obsolete, can't be moved to a new/different vehicle, can't be easily updated with new/improved features and maps, and typically lacks the sophisticated and advanced features of stand-alone units.  I recommend against built-in GPS, for those reasons.
• Does the vehicle provide dynamic seating?  Some vehicles allow bench and bucket seats to be folded flat, or in other configurations, to allow carrying large, long, or awkwardly shaped cargo.  Take note of the maximum length of a board you could fit completely inside (with the doors closed), as well as the width of the trunk or rear hatch.  A standard sheet of plywood is 4' wide, and must fit inside tipped at an angle, even in large SUVs.
• Are the common controls easy to reach for the driver?  While driving, you will inevitably need to turn on the windshield wipers, adjust the heater controls, change the radio station, etc.  Ideally, the controls should be in comfortable positions, and be easy to use while keeping your eyes on the road.
• Are you able to see clearly all the way around the vehicle?  In the interest of style, some vehicles such as Nissan 350Zs, Hummer H2/H3s, and Toyota FJ-Cruisers have dangerously short rear windows, providing only a tiny field of view in critical directions.  Other vehicles, like Jeep Wranglers, mount things like the spare tire where they obviously obstruct the view out the rear window.  Take these factors into consideration.
• If the vehicle is 4WD, is the transfer case selection controlled by a switch (electronic or vacuum), or a lever?  The switches add unnecessary complexity and extra components [to break], and have little positive advantage other than aesthetics.  However a physical, manual lever will be far more rugged, provides positive feedback about the status of the system, and immediately changes the status of the system (no more waiting for the blinking 4WD light to decide when it wants to come in/out of 4WD).
• How slanted is the windshield?  The more sloped the windshield is, the more it will safely deflect rocks and road debris without damage, and the more aerodynamic (fuel and power efficient) it will be.  Vehicles with more flat, more upright windshields, like Jeep Wranglers take a lot of abuse from rocks, bugs, and road debris, and are less self-clearing in inclement weather.
• If the vehicle has computer readouts, such as MPG, compass, temperature, etc., are they in a convenient place and functional for your needs?  Some are capable of displaying multiple pieces of information at once.  Are you able to display the pieces of information you want, at the same time?  Nifty functions are useless if you don't have easy access to them, and are frustrating and dangerous if you constantly have to press buttons to access them again.
• Does the vehicle have more than one trip odometer?  A good habit to get into is reseting one trip odometer every time you fill with gas.  This allows you to know how many miles you can go on one tank, how far you have left to go before refueling, and will alert you to problems if fuel consumption changes.  The second trip odometer can be used to track oil changes, by resetting it after every oil change.
• Does the vehicle have a fullsize spare, either standard equipment or as an option?  A fullsize spare will allow you to continue your journey and have a flat repaired at your convenience, where a "donut" (emergeny spare) will only provide enough mobility to get to the nearest service station.  A fullsize spare also allows you to rotate the spare in when the tires are rotated, effectively giving you 25% more life from your tires, but costing 25% more to replace at the longer interval.
• Does the vehicle have a rear window wiper and defroster?  Both can be tremendously helpful in inclement weather, or cold environments.
• Does the vehicle have sufficient cargo areas for what you commonly keep in your car?  This includes things like cup holders, map pockets, places you can tuck your toolbox, room under the seat for an ice scraper, a place to keep your cell phone charger, etc.  Think about what is in your current vehicle, and where that stuff will go in your new one.
• Does the vehicle have a roof rack?  If so, how much weight can it support and how will you load it and secure gear?  We all end up needing to carry large items, whether they be moving boxes, Christmas trees, or vacationing bags.  Where will these items go?
• Is the vehicle available with a trailer hitch, or do aftermarket companies manufacture one?  Trailer hitches have many valuable uses, including carrying a hitch-mounted cargo basket, pulling a recreational trailer, a connection point for recovering a vehicle stuck in mud, and protecting a vehicle in low-speed collisions.  A good hitch, plus the trailer wiring adapters, typically cost a couple hundred dollars from aftermarket sources.  Some vehicle manufacturers offer them as upgrades at a reasonable price, and it will be covered by the warranty.
• Does the vehicle have any extended warranties that might usefully apply to you?  While most of the warranties seem like a "scam", some are surprisingly good values in certain circumstances.  For instance, starting in the 2010 model year, Chrystler/Dodge/Jeep offers a lifetime bumper-to-bumper warranty for only $2500 (for as long as the original buyer owns the vehicle)!  Jeep is going to fixing my Wrangler for decades.
• Are upgrades available piecemeal, or only as larger packages?  Some vehicle manufacturers only offer upgrades as part of larger accessory packages, and often the assortment of additions are completely illogical and seam like they were picked out by throwing darts at a dartboard.  (Realistically, they were picked out by some bean-counter as a way to minimize assembly-line cost, and squeeze extra money out of you when you attempt to get a couple specific extra features you want.)  However, most dealers are able to order and install single upgrades, after the vehicle has arrived on their lot, as you desire.  Also, beware of dealers that intentionally add extra features to make money, because they fetch a premium for doing this.
• Do the seats and controls adjust enough for everyone in your family?