I’m seriously considering this.Question/reality check: Does anyone see a downside to this scenario or would advise me to navigate the waters differently?

Unless you're writing the offer as the licensed person on the other side, hire a good Realtor to help navigate the situation and work with him (whether he's a good guy with one crappy review, or a crappy unethical one). 

How you'll get the most out of BiggerPockets is to understand how to navigate through it and understand that it's a two way street.

Thanks man, I'm new to the site so just learning how to navigate everything.

From working in financial consulting and asset management at a real estate investment company, to serving as a consultant in a government contracting capacity, Kevin has acquired a broad array of skills and experiences with which he plans to use to deliver exemplary service to his clientele.While passionate about real estate and helping others navigate the real estate transaction process, Kevin makes it a priority to designate time for the things that matter most to him.

I'll say too, my opinion of HMLs has changed over the years, they all aren't loan sharks (but many are) and there is a real lending niche they serve, especially for flippers. 

You should do your own research, but if you trust your realtor enough to help you navigate this transaction then you should also trust their title company.

The competition seems stiff, and with so many sharks out there sniffing out what deals may be, I'm trying to wager whether this is a game that I can bring value to and/or any edge that would make it worth the energy.Don't get me wrong, I'm 100% open to F&F's in this market (or B&H's), but I know that I need to know the rules, stakes and potential benefits before playing.

(By the way, there are legal exceptions- that is another story and difficult to navigate), Now not only does that inhibit a growing and vibrant economy but for this to happen as a result of a law to "supposedly" protect the consumer is absurd!!!

The fate of future Thanksgivings was determined when the op rented to family.Attempting to navigate this situation without an attorney is asking for trouble.