Id more or less like to own the properties and then hire out the property management either internally or externally 

No one can or should tell you what to do here because theres so many internal or external factors.

I am currently listing it with the IMLS as well as 6-7 individual websites focused on international/panama real estate.

Is that old-fashioned of me?

And she has international clients.

Since it is kept internally. 

Keep things simple, do not create any payroll for him and focus on making more money.Now, if he makes $75k net, which is after expenses - then he needs to consider an S-corporation and W2 payroll for himself.Bookkeeping is simple, really: record everything he spends for business in any form that is simple for him: old-fashioned notepad, Excel or Google Sheets if he knows how to use them or apps like Expensify or TaxBot.

It's the INVESTOR that either cash flows or Not.I do want to address something that seems to be a problem with most investors (if not all) who do not use Future Value formulas like the Internal Rate of Return (IRR) in a spreadsheet.Many Investors don't really think of Cash Flow as anything but your Rents minus expenses.HOWEVER, the reality is that Cash Flow is really something VERY BASIC.

@Jamie Briscoe Cash on Cash Return, there is an Internal Rate of Return however I don't have a strong grasp of the ins and out on calculating it at the moment but there is an article about it here on BP that I found:https://www.biggerpockets.com/renewsblog/2010/09/02/introduction-to-internal-rate-of-return-irr/

I anticipate the internal box temperature may reach 800 degrees.