2) I'm thinking of assigning the agents to strictly do sales or management only.

Many states are very strict about security deposits, sometimes with triple damages.

This was a VA loan, so I assume they were being too strict with the requirements.

Should I strictly shoot before and after content, or some during rehab as well.

If you go that route you need several documents to protect you and effectuate taking over mortgage payments (POA, notice to release, etc. )If you only have a strict 90 days to do this then in your agreement that should be spelled out but several things depend on your relative and how secure he wants to be in the fact that you will basically hand the house back over to him at the end of 90 days if you haven't sold it.

and yes City of Portland is extremely strict with the short term rentals, they even go on the airbnb website to look for operators without a permit.

Account ClosedSeconding the concept of "just don't go there".IRS rules are strict about avoiding any direct or indirect transactions of provision of benefit between and IRA and a disqualified party, in either direction.You and any LLC you own are disqualified to your IRA.The IRA may not lend to you or any entity owned by you or a disqualified party.The penalties for engaging an a prohibited transaction are severe, and not worth messing with. 

If in doubt you should always default to no, but that doesn't mean you should strictly forbid it.

Traditional banks have strict guidelines they must follow regarding income. 

@Scott SmithYou have the option of creating an qualified opportunity fund and investing in the qualified opportunity zones.There are strict rules on where you can invest in and how much improvements you need to make to the investment property.