Seven Stroke Roll has excellent advice, always be looking for a field! Instructors probably have good ones spotted in their habitual cruising areas. The Tug pilot before being turned loose to pull up gliders is shown suitable fields near the launchpoint. The unfortunate Australian who pulled the chute and plonked it into a nice big paddock, had to make his decision above 2,000. Wait until you are too low for the chute to deploy and your goose is properly cooked. And above 2,000' it is difficult to see the ditches.
Glider pilots must do field selection as a vital part of training before going X-country. In fact it is recommended that they study fields when driving the car round the countryside. The glider is much much easier to manage when landing in a field; when getting low, you have chosen a suitable area by 2,000', when getting lower you have chosen your field - by 1,500', and are still groveling at 800' on the downwind leg hoping to climb away. Which adds up to a lot of time lingering in the air, assessing the wind direction and strength; discovering problems with the chosen field (horses? flooding? rocks?) that may not have been noticed before....and giving you a chance to choose a better field nearby.
We also train to assess the height above the ground without reference to the altimeter; if the trees are rising up around you and the cows getting bigger, etc.
The glider is also designed to land in a field, even a brown muddy field in November....without damage or injury. They seldom turn over in a field landing. Power aircraft often do. Field landings in power aircraft more often cause injury and damage; the main thing is to arrive in control, at the slowest sensible speed, even landing on a house or in trees you can walk away from an engine failure if the approach has been properly controlled.
I think that if you have the money, a Cirrus would ease your mind. Especially in the US, where if you kill or injure yourself or a passenger, the lawyers will be queueing up. Not many power pilots have cross country gliding in their logbooks, it could make them safer pilots altogether.