Most buy the entry level SFH because its what they are qualified to purchase.  

You can offer to buy these properties and assume the existing loan.  

Buy if the numbers work.

You can't directly do something to allow you to sell the flip, and buy the triplex without paying gains. 

Both of these allow you to low down payment loans to buy a primary residence with fixed interest rates.

@Cameron Porter half off of a $30-40K price may not be enough to make a purchase work.We've seen clients quickly get upside down with Land Bank purchases:(So, proceed with caution and hire a great inspector and contractor to go thru the property before you agree to buy it.

.: So in 25 years people that buy now will be glad.

By the time I was ready to jump back in and buy again rates had shot up as had prices.

@Sean Dillon figure out how to buy a 2-4 unit with FHA loan.Then rent at least one of the units long-term for stable cashflow.Try STR in another unit as well as the other bedrooms in the unit you live in.You may even consider living in the basement, attic or worse unit in the building to rent everything else out and max cashflow. 

In depth knowledge of a city's economy is not necessary if you are buying a single SFR.