I assume with the experience you have there has to be at least a few good reasons to advise him to do the opposite of what you would ordinarily advise against.  

@Stephen RogersHere is what I found on the Realtor.com site```````````````````````For MS only...GUIDELINES FOR UNLICENSED PERSONAL ASSISTANTSMREC list of activities that cannot be conducted by an unlicensedpersonal assistant.Guidelines for an Unlicensed Personal AssistantAn “Unlicensed Personal Assistant” who works exclusively for alicensee will ordinarily be an employee rather than an independentcontractor under Mississippi and Federal tax, unemployment andworkers’ compensation law.

If you live in more than one place—for example, you have two homes—the property you use the majority of the time during the year will ordinarily be your principal residence for that year.If you have a second home or vacation home that has substantially appreciated in value since you bought it, you’ll be able to use the exclusion when you sell it if you use that home as your principal home for at least two years before the sale.$500,000 Exclusion for Married CouplesThere are certain additional requirements you must meet to qualify for the $500,000 exclusion.

Because it's family you probably won't have any court issues regarding that but ordinarily it could be.

There is so much money backstopping the banks (protecting them) that things banks ordinarily would not do, as being too risky, are no longer risky to them because the government protects them and insures them3, Bankers make money in exotic derivatives like Mortgage Backed Securities, (MBS) Collateralized mortgage obligations (CMO) and tranches rather than in lending and banking services.

Ordinarily, when an investor sells appreciated assets such as stocks, bonds, or real estate, he or she is faced with Federal Income Taxes on these gains, at the flat tax rate of fifteen percent (15%), in addition to State Income Taxes on the gain that vary from zero to 9%, for an overall tax rate between 15-24%.

These will ordinarily be in smaller markets but not necessarily far away from large metros.

They can use their cash to purchase a money order and deliver that to you in whatever manner you ordinarily receive non-electronic rental payments, like a dropbox or by mail.

Ordinarily, you would have to file a separate return for your business (or businesses).

Review Page 3 of IRS Publication 598, which states: “Business activities of an exempt organization ordinarily are considered regularly carried on if they show a frequency and continuity, and are pursued in a manner similar to comparable commercial activities of nonexempt organizations.†An example is given in the publication.