Simply gifting him half the property now wouldn’t immediately allow him to claim the exclusion without fulfilling this residency requirement, I don't believe.One thought would be to use a HELOC to pull just enough equity out of the current home and use it to buy a smaller home, or at least the down payment.

While they might not be the cheapest - no HM lender is "cheap" - they do a good job at what they do.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

All good, he got the job and started on May, 10, 2018.To make a long story short. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Professional property managers stay updated on legal requirements through memberships in state or national organizations.

Nice job! 

@Andreas Mathews admirable, but make sure you do some research so you understand what a PM can make.Starting your own PMC business will require 75-150 doors to make a decent living, depending on gross rents and your fee structre.Working for a SFR PMC as a PM, will require a RE license and you usually get paid a percentage of the gross rents the portfolio of owners/properties you manage generates.

I am considering getting into this space (looking at some courses), but worried that its too late, and that deep local market knowledge/understanding of buyers/connection with developers etc is required to make this work, which only incumbent/long term investors will have and would be hard for a new entrant starting from scratch to catch-up...is my hypothesis valid in your opinion ?

Additionally, we have developed templates for tracking key metrics that we require our PMs to fill out weekly.