I advise to leverage your current skills to work in other trades and get into real estate investing once you're ready.

Contact the Federal Trade Commission and the Consumer Financial Protection Bureau. 

You offer him $200k made up of the $50k land lot in trade subject to the existing $150k mortgage.  

Yes, but the trade off is worth it.

I've been an entrepreneur for about 15 years now and since my first adventure as a entrepreneur was in a construction related trade, I consider myself very handy and somehow capable to deal with contractors.

It sounds like the ONLY benefit in this deal is the 0% carry-back and you are trading that for a reduced rental rate renting the property back to the family member.

I have been the Jack of all trades in the real estate industry.

It's a jack of all trades here with little to no trade offs/cons when comparing apples to apples to other large STR markets.The key to success here though comes in the knowledge and execution.

For example, a job with a builder will expose you to lots of things: land acquisition, new construction, renovation, trade experience and contracts, financing, permitting, etc.

I'm thinking 7 years + to trade equity, 12-15 years for material wealth generation.