I think Bill Gulley mentioned how to gift a % of property ownership year by year so that the gifting per year never reached the taxable limit.

Cheaper the better, and more time saved the better.

Check this article on "imputed interest"Tax Rules on Imputed Interestby Eric Bank, Imputed interest is taxable, just like real interest.Your business might incur imputed interest in several ways, including installment sales, below-market loans and original issue discounts, or OIDs.

Good news everyone, the $500 de minimis safe harbor limit was increased to $2,500 for taxpayers who place property in service, that are NOT required to produce an audited financial statement(applicable finance statement).Effective for January 1st 2016 they are adjusting audit procedures to ignore items below this threshold provided provided you have a receipt.This means you will not have to depreciable items below this threshold as long as you elect that safe harbor.Of course it was released this morning, after I prepared for my presentation this evening.This represents HUGE $$$ savings and time savings.IRS Notice Notice 2015-82This Notice is effective for costs incurred during taxable years beginning on or after January 1, 2016.

Even if it costs a few bucks, it's cheaper than learning the hard way.4) Do not worry about what happens if the boyfriend moves out.

If rentals get tied up in that S-Corp, you'll have tax problems - mainly the fact that you can't get the rentals out of the S-Corp without creating a taxable transaction, even if you want to move the property back into your own name. 

Also, when calculating repair costs, you have to add a disclaimer to your marketing because you may have a contractor look at a house and give you estimates based on cheaper quality materials, appliances, or finishes, while your end buyer may spend twice as much to have it look the way he or she wants.

In LA, nobody pays 550/sf for 350sf, they tend to be much cheaper.

With a self directed IRA, you expand the investment choices beyond just what Wall Street sells, but it is still hand's off money until you take taxable distributions to yourself after age 59 1/2.A ROBS plan would not work.  

I might do a little more research to see if there are any cheaper options, but this doesn't seem to be too mainstream yet.