The other option was that he hired a contractor that took him to the cleaners.

Dave NA ,That is correct that if it happens after it was the residence, yet they would STILL have depreciation recapture.I would still sell and buy another if it all possible as you would have a cleaner basis for depreciation.

.- my painter/drywall guy/cleaner husband/wife team, who charge me the same whether it takes 1, 2, or 3 coats of paint to cover the nasty colors a former landlord allowed- the floor refinishing guy, who has done a good job on 8 or 9 floors this year.

A short sale or deed in lieu of foreclosure would be much cleaner and the borrower/friend could get a signed agreement from the bank that they would not proceed with a "Deficiency Judgment."

That does not make them investors any more than the guy working the counter at the dry cleaners he owns.For a real investor, there would never be a consideration to quit their 'day' job and work in their real estate.

Yep, that would be much cleaner and easier.

If the development is residential, how long do you think it'll be until there are dry-cleaner, insurance agent, restaurant?

While this is a common matter, it's still a slight issue and asking the title folks to do their job and provide a cleaner commitment is not being difficult.

Also, you'll have one lender managing the proposed transaction, coordinating requirements on all the properties, appraisals, inspections, engineer reports if any, title work, escrows, insurance and closing requirements, it will be much cleaner to facilitate with multiple properties.

Cleaner.