I would focus on the battery. "kinda sounds like it's turning over" could just be a bad/low battery. The tender (depending on what brand) could be just not charging it. I would take the battery to somewhere and have it tested, it's free usually.
The starter squeal can be fixed, there is a video on youtube for this and it's cheap.
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2000 Boxster Tiptronic
2003 Boxster
2003 996 C2 Cab
2002 996 (SOLD)
1986 944 (gone but missed)
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