It's possible she has some dimentia going on as well. Hard to say. She used to be trained to go in a litter box when we weren't home, and we could leave her loose in a large enclosed area - like the entire kitchen.. or the living room. Those were the days. She was easy to train, actually, and she peed in the litter box for several years with very few accidents. About a year or so ago, she just stopped peeing in the box and started peeing errantly around the house instead. i tried to go "back to basics" with her and train her the way I did the first time, and she never was able to do it again. Since then we've have numerous strategies for how to keep her during the day when we're at work: a large ex-pen with the litter box and a bed inside, a large crate with a raised floor and dog litter underneath, tried different parts of the house, etc etc etc… all the same. We are now using the large crate with a raised floor, pee pad on one end and dog bed at the other end. She gets it about half the time.
I think the root of her fear is that she hates being pilled. I have always approached with a very matter of fact attitude toward her - not coddling her when I do it... kind of like 'hey, you need this, so come here'. Trying not to make it a big deal, or act like it was some awful thing. But she hates it. And I think it has made her afraid and wary of me. I've tried every possible way of pilling her to make it less traumatic, but she is expertly skilled at picking out the pills from whatever medium I hide them in. The only thing that has worked consistently is to ball them up into cream cheese, pry open her mouth, wipe the ball of cream cheese on the roof of her mouth and then hold her nose toward the ceiling so she swallows the ball. There will be spurts of other things that will work, but we always come back to the cream cheese.
We do have a fenced in yard, but we live in a city so I'd be wary of allowing them to be in the yard when I'm not home all day. I'd be afraid they'd escape, or someone would take them, or the dog next door would escape from their yard and dig into our yard (which has happened before and Lenny attacked him right as he got his little head on the other side of the fence, quite scary actually). Lenny doesn't need to go out often - he's like a camel - he could hold it for 3 days if it was raining or snowing out.