You want to buy a 944 because you feel your Boxster breaks down too much? What is your second choice a Range Rover?
Whenever I visit my Porsche mechanic there are two things I can always count on seeing, old tires in the back and a 944 in for repair.
You must not have had a very low mileage 944, or a very looked after one?
Boxsters/Caymans and water-cooled Carreras are reliable cars but they are not durable.
And Porsches that are 11 years out of warranty with moderate to high mileage are generally not durable anymore.
If you want a low-maintenance car for autox/DE, get a Miata. Selling mine was the bigget mistake I ever made... I should have realized this when the buyer flew up from Florida and drove it right back down from the airport. Like perhaps your situation, I should have kept the Boxster for street and Miata for autox/DE. I beat the snot out of that car, it cost nothing to modify (compared to Porsche), tires were cheap, and it never, ever, missed work. Asking an old Porsche to do double duty means your wrench box and wallet are going to be very busy.