Maybe you'd benefit by taking about ten (10) steps backwards.Forget decedent's estates.

I've had pretty good success charging my tenant's benefit cards (MasterCard stamped).  

If a multi family is financed under the terms of owner occupancy, will the tax benefits still be in effect?

This is a post-tax retirement vehicle (meaning you don't get a tax deduction for contributing like you do to a 401k or traditional IRA), however you are likely at a very low tax bracket so wouldn't get much benefit from a tax deduction right now anyways.  

Unless you want to file employer taxes on them, give them benefits, tools, unemployment taxes when they quit/get fired, liability insurance, safety equipment etc etc.

I think getting into the trenches now with a mentor would be a great benefit to you.  

However, here are some random thoughts:If 60% of rental income provides sufficient retirement income, you can probably afford to do nothing :-) This has the added benefit of continued capital appreciation, relatively easy single family home management and tax free stepped up basis on first death.

They are more likely to work with you if you're of immediate benefit to them. 

The benefit of putting a property in your wife's name is for accessing financing later.  

@Brandon Crumpton - Great question and @John Thedford summed it up nicely.Yes, it's a double edged sword that enables you to take massive leaps forward and risks or can be utilized to the point where you overextend yourself and then being unable to sleep well at nights.Use leverage wisely and you will benefit from it's advantages positively.