I don't know that I have much to contribute, but I'm definitely interested in the same answers on the same time frame.
Be forewarned, there's a strong and vocal contingent on this forum that will denigrate and demean you for playing these games. They seem to feel that if you're retired early, you shouldn't qualify for any need-based financial aid regardless of what income your tax forms show. For example, you can qualify for the simplified FAFSA EFC calculation if your kids qualify for free or reduced priced lunches (where I live, this is done for under ~$50k of income and there is no asset test), but we've had numerous threads full of hate for people who get reduced price lunch based on low income in retirement.
The FAFSA parental asset test assesses ~5% per year of your assets over about $40k (depending on your age and number of kids). So if you have $400k in non-sheltered assets, say from a taxable brokerage account you intend to use to fund the first 5 years of your Roth IRA pipeline, then each year they will take 5% of the remaining $360k, or $18k. I'm obviously simplifying the math a little.
The FAFSA income test assesses all income over about $30k (depending on your age and number of kids) at 50%, so even a $70k/year job means you get zero aid if you have several hundred thousand in non retirement assets. $70k/year of income with $30k of that excluded means you are assessed 50% of the remaining $40k, or $20k on top of the $18k from the preceding paragraph's asset assessment. Together that's $38k of EFC, which is more than the CoA at virtually every school that uses the FAFSA.
There are lots of different ways to take yourself totally out of the running for the FAFSA, but $400k of assets and showing $70k/year is one way to get zero aid. Basically any income over about $30k/year and any nonretirement assets over about $40k will count against you, at 50% and 5% respectively.
For this reason, it's generally speaking the income test that is the killer because any income you show on paper is effectively taxed at 50% up to the full CoA. Having one working parent, or doing annual Roth IRA pipeline rollovers, means that schools will just take half of your income instead of awarding financial aid.
Then there are a TON of gotchas hidden in this process. For example, the previous year's retirement contributions count against you as income (assessed at 50%) even though retirement assets don't. The assessment exclusion values change every year, based on your age and the number of kids you have in school, and annual adjustments to the system. That makes it virtually impossible for us to discuss viable strategies, because what works for my family with 3 kids at 39 years old will not work with your family with 4 kids at 40 years old.
On the other side of the equation, the ACA income limits are also a disaster of local regulations. In Washington, the family income limit for free healthcare for kids is something like $75k per year if you have three kids, but it's only about $45k/year for the adults if you have three kids, which means there's this donut hole where your kids are covered for free, but you're still required to buy a whole-family plan on the ACA exchange to cover the parents, which then double-covers the kids. But generally speaking, the limits line up pretty close to the FAFSA limits at something near $50k/year of income (in my case).
So for my situation, this means I really need to get my retirement income on paper down under $50k/year. Like you, I have rental properties, but I'm probably going to sell them, after we quit working and before our first FAFSA year, in order to minimize capital gains taxes we would pay if we sold while also working, and to not show those capital gains as income on the FAFSA. We'll take all of the equity from the sales and sink them into our primary mortgage, because your primary mortgage is not a FAFSA assessed asset. Without a monthly mortgage payment, we can easily get our annual spending down under the ~$50k/year level required for both the FAFSA and the ACA, and can thus make <$50k annual Roth IRA rollovers as our only source of paper income.
Brooklynguy and I have had many public discussion here about why I plan to do this even though it is a mathematically sub-optimal strategy to pay down your primary mortgage instead of investing that chunk of cash in the stock market and just make the monthly mortgage payments from that investment. But the ACA and FAFSA just throw the whole thing into doubt, by requiring that you show a minimal amount of income to qualify for any benefits.
And don't even get me started on the CSS profile or the 26 colleges in the 568 President's Group, which use entirely different methods. They both count home equity, but are slightly less punitive of parental assets. You need to figure out where your kids are going to apply.
Wow, that was a lot of confusing content in a hurry. I'm happy to explain any of that that didn't make any sense.