Assuming this is one of your first potential flips, the IRS wouldn't consider the flip to be part of a trade or business yet (recharacterizing the asset from an investment and changing the tax consequences). 

But I think his hard work and rental history is at least enough to see if he's got a chance to actually own an asset with equity and continue paying on the note.

Fees paid to obtain the new mortgage aren't deductible, nor can you add them to your basis in your home.

Tenant understands and agrees that Landlord has no obligation to obtain insurance for Tenant including, but not limited to, liability, hazard, or contents insurance.

With real estate, ostensibly, you own a house, commercial building, apartment complex, land, or some other tangible asset.

These DSTs cash flow at projected rates depending on the asset class and debt load.

I am constantly finding properties in the ghetto that have been purchased by someone's IRA for a ridiculous amount of money ($60k-$70k when the house would only sell for $10 to $20k at the most).There is no asset management in place.

$2,000 rent on a $180k asset sounds about right from a cashflow standpoint.

Large size creates extraordinary asset and sub-market diversity.Sub-markets!

Or for that matter you could stay together and do one exchange into another asset.