I would like you guys' thoughts on my options these next few years given our situation, which is not ideal but better than that of a lot of people in the US. We live in a LCOL larger city in Alabama. I'm 54, wife is 52. This is maybe a bit long, as its more vague, sort of "what do I want to be when I grow up"

- I'm 10 years into my third career, currently making only $75k. I took a big hit couple years ago from losing a job where I'd recently cracked 100k.
Could make a good bit more moving but tied to this area for a bunch of reasons including two widowed mothers. Could close the gap some more even with staying here but after getting badly burned previous job am seriously cautious about company culture and stress level (last job making me sick, actually had an afib episode -- fairly healthy otherwise). Current job is tolerable, but would like more time off (was nearing 4wks at old job, now back to 2wks) Am putting 8% in 401k (company typically matches 50-75%, no cap). Family health ins is $925/mo pre-tax.
- Wife is a teacher in catholic schools, having retired from public system after 28 years (burned out on ever increasing red tape and worse students).
She already draws her teacher pension ($30k) and gets about $40k more from current job (catholic pays less than old public school job but much better quality of life). I will get all of that pension if she goes first (we picked payout option w largest survivor benefit since we're close in age). She *is* also covered by Social Security. FWIW Alabamas state teachers retirement system pension fund is in good shape compared to a lot of states. At no charge her state retirement pays for a Supplemental Medical plan that covers almost all copays and deductibles from my primary plan. When hit 65 there is a cheap Medicare supplement. Alternately IF she works at a place where *she* has no insurance option, say drops back to part time , then we can both get on the retired teachers nice primary medical for only $700 ( and I can stay on if she passes first). FWIW her insurance while still employed in public school was only $325 for family -- knew we had it good but did not realize just how sweet until she retired.
- Only son graduating from college May 2020 (computer science). I got a couple small federal loans to help cover his room and board first two years (he chose a local university, we wanted him to still have college experience - independence was really good for him), -- I have already paid off one. Son had scholarships and small loan each year in his own name for rest - would like to help him pay those off faster if can. Once he's off our health ins we could possibly have two single plans, w total cheaper than 'family' (neither of our employers has a Plus One option).
- Modest house paid off a couple years ago (~$150k). No car notes (though prob need replace one vehicle in just a few more years). No credit card debt, although (I will occasionally use a 0% offer for a bigger short term expense and pay off in the period).
- I have $335k in Schwab Rollover Trad IRA and a Prinicpal 401k (w current job). Know I should have more by now but life has happened along the way. Should be an ok amount if can leave untouched another 10 years or so, assuming so-so 4% return. What's funny, I've done the spreadsheets, and a 1% swing in average yield dwarfs what I'm likely to be able to contribute over the next 5-10 years. Not sure how to count the wifes $30k as a retirement account equivalent -- if considered as a static amount and siphoning off a fixed yield indefinitely (pension has no automatic COLA), then 5% gives $600k equivalent PV, 3% gives $1M equivalent PV (of course no leftover value once we both die).
- We have about $30k in ready cash for emergencies outside of the 401k.
Punchline...
All common sense says keep working, both of us, but {edit by Moderator Jbranx} we're both sort of burned out and don't want to keep going full steam for 10 or so more years. Her pension by itself is not enough, so quitting outright is not an option, but the guaranteed seat at the employer group health insurance table, opens up options for possibly dialing back work well before 59-1/2, 62, or 67 much less 70.
She could work part time, OTOH how easily can she make something approaching her current $38k and still have all that teacher time off?
Other option for me is to transition to remote contract work (I'm a programmer in my 3rd career) and decide how much I work, but that's scary as I've always been an FTE somewhere. Another option - I have 6 years service on the books in the state retirement system myself (taught as a full time univ CS instructor in early 2000s). If I could get back in for 4 more years again I could buy back my six years service to hit the 10 year vested mark (start drawing at 62). But that still sort of a real job, still w some different stress. OTOH I could just teach some adjunct courses if wanted to stay part time.
Your thoughts? Anybody else done anything here similar? Successfully chosen more time off and keeping expenses low? Downshifted before fully "retiring" even though nest egg not as fat? I know this is awfully vague. Thanks anyway.
[FWIW I find annoying the 'I retired in my 30s' blogs where the couple a) was each making 6 figures in their 20s, b) blew off ever having kids, and c) are still working some, just not full time in a cubicle. ]