...Don't let the fact you can't afford a Beech Premier jade you into believing GA has zero transportation value. There's several iterations of mission sets where a piston single engine is a substantial time and money saver for the individual that puts a dollar sign to the idea of not getting to one's destination fatigued as hell.
I did it for a year in a warrior II. The block time for me was 4.5 hours. Driving would have been 9-10 hours (and that's solo driving, wearing diapers and not eating on the way) depending on traffic and weather. That's a non-starter for every other weekend. Airline was 8 hours (no direct flight) of which 3 were driving to the nearest class C commercial airport. More expensive than flying the piper per round trip by double and couldn't be price matched for deciding to travel on a whim.
I rather fly for 4.0 in a warrior than drive a car for 10 hours every weekend. No contest, not even close. And I did that right after work. If I had pulled that stunt driving 10 hours right after work for a year, I would be dead somewhere on an East Texas country road today, no question about it. If you need the same level of active attention and control manipulation in cruise flight in a piston aircraft as is normally required while driving in highway traffic, you need a xanax prescription and a rubber helmet, not a faster airplane.
As to headwinds, I flew over west Texas going west all the time, never encountered 60 knots headwind. I had all Sunday to get back. Winds looked stiff? I departed a little later, presto problem solved. I have an IFR rating and no aversion to flying over the Edwards Plateau and TX Hill Country at night. My wx dispatch rate was 100%. Meh.
300NM is a joke. The OP already has too much airplane for that mission. The only mistake he made was not getting a C182 or Dakota instead of the 235. Both 10 knots faster for one less GPH and no gear mx. Even then, he's ahead versus driving, unless they built a direct route concrete road for just him
.