In regard to crypto currencies...I would say that there are siginfant risks associated with investing in crypto currencies.  

Since all these 4 entities will have a tax id associated to them, I am trying to figure out if we will need to file taxes for the 3 trusts, or just the LLC. 

I'd suggest connecting with some of the local REIAs/RE Clubs in the area, like the Seattle Investors Club, Real Estate Association of Puget Sound (REAPS), Fixated on Real Estate (FORE), or the Cascadia Investors Alliance, to name a few.With that said--what are your goals? 

With association dues creeping towards 275 I'd like to minimize the monthly spend for when we do rent it out, to get a much higher cash flow.

I've been building my investor database, and within that, I've created an Investor Pipeline that associates each investor into a stage of our communication, in addition to an assigned probability for landing that investor.

The costs associated with the property are also considered, and with no mortgage, it sounds like you have very solid positive cash flow. 

People want to be paid for their time.I think people automatically jump to negative thoughts abut paying for mentors because of the association with "*gurus* 1 hour seminar make a million dollar" ads. 

It seems that both situations have their challenges, risks, tax consequences, and costs associated with them. 

@Dustin Kooy Have you tried the property managers on the National Association of Residential Property Managers (NARPM) website?

A property that brings in 2K per month and has a 1K monthly PITIA payment (principal, interest, taxes, insurance, association) has a 2.0 DSCR.