So he wants to avoid his 25% tax bracket when putting the money in, because he's much happier paying the 10% tax bracket when he takes it out.

If it comes to an eviction you may be happier if you have a pro dealing with it

No joke.I was fortunate enough to be able to cash out from a house I owned in East Austin, used that money to buy 2 rental properties in cash and also lowered my primary mortgage by over $500.My wife and I couldnt be any happier.

I would be much happier working my current job 1-3 days a week (earning ~$40/hour), which is realistic as I work in healthcare and per diem work is common, and supplementing that with income from other sources including real estate investments. 

that may be hard.I suggest that you talk to brokers, they would have places that are ready for a new owner to walk into, I would also suggest that you switch from"multi-family" to a condo (or two) that you buy and make positive income by renting them.Also, I would worry less about the taxes and more about the cash flow, including all the expenses and the existing rent.. if I pay high rent, but I get a lot of cash out of it I am happier then paying low rent and breaking even.

I'm not saying that I will leave my money in there for the long run, but I am happier knowing that it is making me $0.36 per share every quarter.

And central AC makes for happier tenants.Regarding, washer/dryers, I vote no for the actual appliances. 

I feel altogether happier and more optimistic than before.

I do think I would be happier a little more north.

When I stopped caring I became much happier and more successful.