I focus on getting the job done,  within time frame/cost, with highest work quality possible.

Looking for a CPA with a focus RE Investor tax returns. 

aren't the 1031 guidelines focused on intent vs hard timelines... and wouldn't he have to show he tried to make it a successful rental but for reasons it didn't work and then can convert to primary?

Needless to say, my real estate aspirations changed.I'm planning to shift more of my focus towards real estate in early 2018, when my three partners and I will officially start an acquisitions and holdings business following the BRRRR strategy.

Debt Service on the property $241,395 @ 25% ($60,348) down is $181,047 or $906/month.Cash Flow = $2,875 - $191.67 - $733.33 - $220 - $201.25 - $201.25 - $143.75 - $906 = $277.75/month...on 5 units...Because I focus on cash flow, this property doesn't initially pass my napkin test but if its under market rents, it might be worth digging into more.

At this stage, he is more focused on deductions than income.  

We can all agree that this is a much easier path that allows you to focus your time & efforts on other things whereas running a full fledged business is a full time endeavor.As an entrepreneur ask yourself what takes more time, effort & work?

Buy and Hold has been my focus for learning but I also know a good opportunity when I see it (if it works out).

But if he is seeking companionship or more, it may be a good idea for you to send someone else to his apt when he requests a visit, or communicate via text or better yet a message system. 

Also consider outsourcing this function and focusing on your strengths.