[jhynesrockmtn]

Welcome. I've had/have both. My first Porsche was a 2001 Boxster S. Fantastic car but a little small for me over time. I needed an inch+ more legroom and it was a daily driver. I then went down a rabbit hole of air cooled cars and still have a 911SC and 914 but my daily driver is a 2004 911 C4S. The 911 996+ cars are larger feeling and more of a GT car which is fine for me.

Drive and spend time with both. Figure out what options you are looking for. Interiors changed between the two vintages you are comparing a lot. The full leather dresses up the 996/986 a lot but overall that interior is pretty polarizing. I like it as I appreciate the simpler style, fewer buttons, less computer controls, etc. We have a 2015 Macan and I still haven't figured out 25% of the buttons/control systems do :-)

The Boxster has a ton of storage for the style of car it is. M97 engine presents different issues vs. M96. The mechanic who did my PPI back when I bought my current C4S said the cars he saw with issues were inevitably garage queens with little and infrequent use. I have used the 911 rear seats for my granddaughter and in a pinch for an adult but if it's a weekend car that may be less of a concern. I'm rambling now. Go drive a bunch of them. They are both plentiful in the used market. Consider stretching a bit for a 2009+ car with direct injection...... Also maybe post in off topic and also checkout Rennlist and post there. They have a more active tech section for the water cooled cars.