If he's called-in to early retire or otherwise let go, make sure he doesn't sign a non-compete at that time. He should have anything he has signed, and is asked to sign, reviewed by an attorney. It's just not reasonable for companies to terminate someone's job
and tell them they can't compete including being hired by a competitor, but they try this all the time in blatant ways and it's not just the old guard companies like HP that do this. I've seen my share of "umm, excuse me but this basically puts me out of business, I'm not signing it" type contracts.
Contract work is not as difficult as it sounds. He already knows the work involved, can do a good job of estimating the hours of work, and getting the number of employees to match that work, and then par for the course is 2x-3x of the salaried rate because a.) the contract can be terminated, no severance, no health care, no bennies, b.) the companies can afford it and are likely already paying that or more for the same contract with HP, c.) he'll need business liability insurance, and slightly more complicated book keeping and tax assistance. It's completely sane for him to ask a company he has a very good relationship "what's in the budget?" if he doesn't already have an idea what this amount ought to be. Don't undercharge. It's reasonable to offer a discount for say 2 or 3 year contracts. If it's hourly, it should be expensive to incentivize contracts.
Anyway, this can also be referred to as "slow retirement" which is a working retirement.
Oh and the home improvement investments seem sane also. They certainly aren't getting done, and will need to be done at a bad time if he does get let go or goes for early retirement.