You've got plenty of points to go more than once, so don't let that stop you. Get going. It gets easier the more you do it.
If you're looking for Thurs-Monday trips, I would not suggest crossing an ocean.
Look on Wikipedia under the Airport name, then look up "Passenger Destinations" That's your list of non-stop flights from your local airport. Non-stops will cut down the actual travel time you spend, since the flights are direct.
Use an Award Booking Service if you don't want to spend the time or effort to maximize your value. Generally, booking domestic non-stops aren't considered difficult bookings, so you can probably do those type of trips without paid assistance.
Good luck.