[Boldin] Create a feature for withdrawal strategy recommendations

I currently work 3 different part-time remote, flexible jobs that add up to about 25 hours a week. I'm sure I'm ready to fully retire, financially speaking, but I'm struggling to figure out: A. How much can I/should I spend each year going forward? B. I have a CPA advising me on taxes, but I'd appreciate your thoughts on the best order for spending - see list of accounts/sources - and an overall strategy. My situation - definitely not leanfire, maybe almost chubbyfire? - 1. 53F, no kids, I have a partner of about a year but we don't live together or combine our finances. 2. I have really good health insurance, at no cost except the occasional copay. This is from a former government employer and is for life (supplemental plan once on medicare). Accounts: $65k - Cash/HYSA $140k - Treasury I-Bonds - about half is federally taxable interest earnings (no state tax) $525k, - 403b - 70 bonds/30 stocks, Vanguard custodial account. I will be able to make flexible withdrawals without penalty starting in January or whenever I quit my teaching job. $420k, -Roth IRAs - 50k I could take out now without penalty, another $120k I can take out in 2 more years without penalty. In VFIAX and VBIAX. $850k - Traditional IRAs in VFIAX and VBIAX. House paid off (worth $500k) in MCOL suburbs, but I'm renting it out now for about $2,800 a month and renting an apartment in the center of the city, where I'd rather live. Breaking roughly even, maybe making a little profit on the house after home expenses and the rent I'm paying out. Some other small accounts, like $50k in an old unvested retirement plan, plus I'll have a smallish pension I'll probably take at 65 (full retirement age), will be maybe $1.5 k a month, plus social security. Not sure how much I should consider it, but I'm also a beneficiary with two siblings of trusts holding real estate worth about $10m. I currently help manage the finances etc and draw a small salary there. This is a job I can't actually quit, even after retirement! When my mom passes away my siblings and I will likely hold on to the properties and divide the rental income 3 ways. Hopefully that won't be for many years. Overall, my investments are close to 60/40 stocks and bonds, more conservative for the 403b and cash I expect to use first. To the questions: 1. I think I can spend up to $80k a year if I want to. But will actually be tough for me to spend more than half of that, even though I'm purposefully ramping up my expenses now (hiring cleaners, enjoying finer dining, traveling often). I grew up quite poor and then was a very, very frugal middle class until now. But I don't want to die with tons of money; my nephews and niece will inherit a trust and won't need it. I want to spend more on travel and experiences in the next 10-15 years while I'm hopefully still really healthy and fit. Does $70-80k after taxes seem reasonable for spending? Too much, too little? 2. Am I right in thinking cash first, then 403b? Using rule of 55, I can start withdrawing without penalty in 2027. Then don't touch the rest of it until at least 60? Thanks for your help and insights. I'm sure there are many things I haven't thought of! I did hire two different fee-based financial advisors in the past 3 years, but they were not very helpful, as my situation is unusual - for example, one advised me to roll my 403b into an IRA. If I'd done so, I would have lost the ability to roll it into my current employer's plan and then use the Rule of 55 next year. If I consult another financial advisor it will be someone who specializes, but I think learning to manage money on my own is the better plan.