My son (age 24) however, is an independant contractor / self employed and is trying to buy a house. 

I looked into this at more than one occasion, because Milwaukee has such an old housing stock, everything is 60-120 years old.Most of the new apartments we see are 4 and 5 star developments with very high rents, this allows to offset the high cost of construction a little better.

Are you self-managing? 

I use a spreadsheet I developed to determine my entry costs, carrying costs, cash flow, tax write offs, appreciation and exit costs.

Oh man- welcome to self management.

Should I play harder and get into land development?  

I'd also suggest self-managing your first property to maximize cash flow and learn by doing for any future investments.

Start with books and self-education before considering any paid courses!

we are build to rent developers in columbus ohio. we a direct builders for investors around the country. we don't sell on the open market we build from scratch and it's very relationship based. it's very different but I would consider us turnkey. we build at 75% of market value with land and investors can refinance out and do it again and gain approx 100k equity each time. ours is an infill triplex in columbus ohio. that's just my 2 cents. turnkey is deal by deal 

I agree that the best way to make money is self manage your short term rental (not AirBNB, that is a platform).