How long can it last? Repair or Replace

Dad_joke

I have a 2006 EX-L with 280K miles. I think the repairs it needs are about equal to the values of van. It is due for timing belt/water pump. The front suspension needs replaced. Rear shocks too. There is a significant oil leak, maybe 2. I took it to my mechanic to have him look at the oil leak. His guess is the aft valve cover or the Vtec module gasket. The RH side of oil pan is wet like the front main might be leaking. It could be the oil pump. We had it resealed (by dealer) when we got the van at 165K. It needs 2 tires as well. At the moment the van runs well and the transmission is functioning well. I have done a couple of drain and fills in the last 18 months. My independent mechanic has told me that it might be time to look for a replacement as he doesn't see the Ody's run well past 300K. What are the end of life experiences of the membership here?
Now is not the best market timing to get a deal on a $10k used vehicle. If we make the investment, I am looking to get another 5 years out of it just because that should be the life of timing belt.