You could find your local wholesaler ( basically what a land flipper is) and ask about what CRMs they are using and also talk CPAs.  

For me, what was talked about above is nowhere near close enough for me to judge or provide an opinion on someone as just because someone changes their name (we have done it several times for different entities) or someone could be co-gp or LP in a deal but not in the limelight) does not immediately set off my radar of "omg this person is not legit or a scam artist". 

Finding an investor-friendly agent is key and they should be able to help you with 1-4, I'd say talking about those questions you asked would be the perfect thing to ask any potential agents you interview! 

Recommend talking to your CPA about this strategy. 

I have no social sphere or contacts family or friends in Oregon (I don’t know anyone besides my fiancée).Goals: continue to have flexible schedule while enjoying what I do (selling real estate) and making good money.

Alternatively, yes you could sell, pay taxes on the gain, and use the proceeds to help your mom directly.Would suggest for you to talk to a CPA and a 1031 specialist to confirm your best move!

I have talked to tons of investors recently and everyone says the Zillows interface is the worst, but it is just a side comment and we keep going on to the next conversation. 

I think you will definitely want to talk to your lawyer because there may be items linked to this transaction you are not considering. 

Clear CommunicationA great contractor is easy to talk to and keeps you in the loop.

Talk to a tax advisor that you trust or know someone personally that has high trust with them.