New RE investing option buy and hold, Please help!

[Josh Whiteley]

Quick back history.

Bought a twin home in oil boom country so pricing is inflated at this time, and will be for many years to come. I have been thinking about this for a while now to see if it would be feasible.

I would sell my property that I live in now and work with a contractor to build a

1. Multi- family property of some sort
2. Duplex or twin home similar to the one I live in
3. A 2 story home with separate entrances (Possibly built so 15+ years convert it into a single home with upstairs/downstairs)

Basically, I am asking if this situation would work.
Sell current home, and build a new home in that half of the property would be rented out and I would live in the other half while being the landlord. Staying within the qualifications of the Lender so that I would be able to make the payments with current job monthly. 300k approx.

This would not only pay for the property by renting it, but would be a nice situation later in life to be able to invest in other properties while getting my feet wet in this market.

If I need to give more information please let me know
Has anybody done this before?

(I have searched and seems most posts are very generic)