When I die, they can keep renting out the properties or move into the SFH, or take the step up basis and sell it with not as high of a capital gains tax hit (I hope they wouldn't choose the 3rd option).

I'm eager to gain hands-on experience and mentorship in this field.

Land doesn’t depreciate, and while buildings require maintenance, they usually gain value as markets grow, demand increases, and inflation takes its toll.Real estate investors benefit from a significant tax write-off based on the concept that properties lose value over time, even as their market value skyrockets.

I want to gain Capitol under my business name.

Even then, if you've built up enough carry-forward losses, a nice capital gain may not trigger any taxes to be paid. 

I believe you were right he would inherit your cost basis, so he would owe capital gains.

From this CT information, it looks like it is an offset against your capital gains from other property, so you would have to find investors with significant capital gains and/or have them yourself. 

Hi Sergio, I think there are way too many variables to be able to gain any real insight from responses here.

I have studied the market there for a bit now and am comfortable with investing with decent Cash Flow and modest property price gains.

Lenders also have interest only options that could help with cashflow especially on acquisitions to allow you to get the listing up, and have your listing gain momentum (some listings start off slow while they accrue bookings, reviews, etc.)