Are there any questions you'd suggest asking to better understand this loan structure and its potential limitations?

I know there are limits on how much you can deduct for each year but my guess is that you would be fine with only one rental.

Between strict public record laws, limited access to data, and the way certain counties handle records, finding motivated sellers can feel like searching for a needle in a haystack. 

.: Getting quotes for the house I'm closing on in April and wondering what to how with for coverage limit and umbrella.

@Tim RogersI believe there are income limits that if you exceed specific income (cannot remember the number) it greatly reduces or zeroes out any deductions from a REPPeople a lot smarter than me can confirm

So it does appear to be possible to get an FHA 203k loan for a 5-unit & convert to a 4-unit.When possible, aim for the Limited (aka Streamline) 203k loan, as it's less complex, not required to get an FHA consultant, etc.Of course, this is based of the two following important assumptions:1)  zoning allows for this2)  and obviously I owner occupy for at least 12 months3)  the total purchase price + renovations are within the FHA loan limits specific to my areaWhat I'm confused about is the timeline or chronological order of the process? 

You're only limited by your beliefs.Practically speaking though, 2-4 unit multi is very very doable starting out, especially if you are willing to owner occupy.

All that said, depending on the size of your RMDs, liquidity needs, and total income, you may consider making deductible contributions to your own IRA ($7k limit, $8k if above 50).

I have around $100K in liquid capital and access to a $50K HELOC at 6% for the next 10 months before it transitions to a variable rate.I have a unique situation where I earn a living through sports betting, which limits my ability to show traditional income growth.

A real estate-focused CPA can help maximize deductions, structure tax-efficient strategies, and navigate complex rules like passive loss limitations and cost segregation.