Fidelity has a retirement planning tool. You can connect your other retirement accounts (and other non-retirement accounts). Then retirement year, when you will collect social security benefits (and what amount), estimated monthly expenses (mandatory and optional).

In a "Significantly below average market" (90%+ of models I hit this mark or better) I should be fine and my portfolio will be about even to age 100. I can't tell it that my mortgage will be paid off by this year but then again I'm not sure how much healthcare costs are taken into account as that is quite expensive.

"Below average market" (75% of models) I slowly increase to double by age 100.

"Average market" (50% of models) it increases greatly to almost 6x my current portfolio by age 100.

This assumes I "retire" at 60 so I can withdraw from 401(k) and Roth IRA and start collecting social security at minimum age 62.

Minimum Retirement Age

Social Security: 62 (30% less benefits)
https://www.ssa.gov/benefits/retirement/planner/agereduction.html

Roth 401(k): 59.5 (Required Minimum Distributions at 70.5)
https://www.investopedia.com/ask/answers/101314/what-are-roth-401k-withdrawal-rules.asp

Roth IRA: 59.5 (No minimum distribution, no taxes)
https://www.schwab.com/ira/roth-ira/withdrawal-rules