The trick is, he doesn’t want to be tied down to his new roommate in case the living situation doesn’t work out.

You should think what can I offer this broker in return so that he or she can teach me the tricks of the trade. 

When you sell, you will owe taxes on half of the profit, plus taxes on depreciation taken previously.Again, trying to hide all of that, as your CPA suggested, is a no-no.Also, the proposed LLC trick won't work.

Banks are not interested in misleading  or tricking anyone.

The trick is to actually have growing income to account for inflation.

The trick will be finding a lender that does not have overlays jamming you up and getting in the way of you accomplishing your real estate investment goals.

@Ryan Tremblay, yes, "combining the 1% rule and the 50% rule is mathematically the same as assuming a 6% cap rate for residential" DOES sound about right - for large swathes of middle America (ie. older homes, in "C" neighborhoods).The trick is to find those sort of deals where the "cap rate" would normally work out to be LOWER than 6% (ie. not so old homes, in "C+/B" neighborhoods).

The REIAs are where old timers, experienced folks hang who know whats working, the tricks that don;t make it into Guru';s talks or books.Best of luck,.  

Also, how was your experience with the bank... did they pull any tricks on you worth hearing about?

The trick here is finding a rep that understands your business and can structure the loans so that they align well with your goals and limitations.