Or would this raise red flags for conflict of interest? 

Are there specific considerations, tips, or challenges I should be aware of in these areas?

Especially a meet up on private lending, ADU additions are discussed regularly (new attendees looking for money for their ADU additions without being aware that no one there will lend on ADU additions).  

I’m aware of loss harvesting when it comes to stocks, bonds, etf’s, etc. but how can this occur with real estate?

Referencing another recent post, there's not a great software solution that I am aware of for on-boarding a new MTR resident.If you aren't already, I would make sure you disclose to a potential resident any relevant issues that are endemic to a unit as early as possible.

So I started with cooperative assignments, which enabled me to raise much needed cash and then branch into other strategies, buy and hold, fix and flip. 

If you only look for the input you want, you won't get the feedback you need.Self-awareness and self-analysis is a crucial part of investing.

As you are likely aware, water can travel great distances from its source, across pipes and beams within the walls.

I am aware that I would have to claim a large gift tax exclusion but $300K is relatively small.3) Use a 1031 exchange to sell this property and buy an equal/greater one in AZ, where #1 son lives. 

If I did have an opportunity, where do I start and how do I raise funds for it?