Hello, I have a few rental properties and I am looking for a program that tells me the overall performance once I input income and expenses.

I assume I need a CFP first to figure out the Roth conversion part and once converted then in comes CPA? 

My wife is also a high income earner--she works in the hospitality and wine space.

With prices as high as they are and income not keeping up I think more and more families will buy property together. 

(Can I use the estimated cash flow of the house as proof of income for mortgage applications?)

You will need to work with a tax professional to analyze your current tax situation (income, deductions, activities, etc.) as well as projected income from the fix and flip business.The benefits have to outweigh the costs (payroll costs, additional tax returns, more stringent reporting and compliance requirements, etc.).One important note - an S Corp is not an entity; it is a tax election.

I was quite surprised when he invested $500,000, and followed up with a $250,000 additional investment the next year.

@Jeff RyersThere is a basic rule of thumb for income qualification but I use an additional one as well. 1.

If not, what are other creative financing types that do not require income verification (or limited verification)?

If that is the case, then the income gets reported on Schedule C.