Thanks for any input you can provide!

The Architect working directly for me will provide me with more leverage and peace of mind. 

This can be done through linking up with local investment groups, or go to meetings that provide such interactions.

Calculator should provide amount of conversion  tax payments needed, one or multiple conversion options,  Medicare IRMAA impacts, various investment percentages of Roth growth vs IRA growth, and RMD amounts with associated tax bill.I’ve seen numerous CFPs hawk their services for $5,000 or more.  

Hi Ayyoub-Great question and I am right up the road from you in Ann Arbor.Certainly, getting a conventional loan may provide slightly better rates than an investment loan like a DSCR loan.However, if you are buying income property you can use the income to qualify for the loan with a DSCR or Debt Service Coverage Ratio loan and not so much your personal finances like a conventional loan.Basically, you need three things.1.

Larger national companies like State Farm, Allstate, and Liberty Mutual are known for providing comprehensive coverage, so they could be good places to start your search.

These syndication can provide an 8%+ cash-on-cash return - providing investors monthly cash flow - and a 15-20% IRR over the length of the project.

Has anybody had a situation like this before or able to provide more color on best approach / details?

I think HH provides these new home buyers the opportunity to purchase a home with some financial flexibility being able to rent out portions for extra income. 

The other 3 above should be able to provide referrals, but don't blindly trust anyone!