Hi, Jaycee The deal makes sense for me after accounting for all expenses including vacancy, cap ex, and repairs.

They told them that this investment will change their life and that money in a retirement account or 401k is worthless.

I recommend finding a real estate and business accountant to help you with filing your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

Don't forget about your property taxes going up to account for that ADU.

How much is reasonable for management, accounting, and rental commission fees?

Problem: Set & Forget - Most people know the importance of an accountability partner when it comes to goal setting.

When they move out, I can access their account to charge for cleaning and repairs.

I think some hosts would account for the cost of purchasing good quality bottled water as well, which is why the Brita water pitcher is popular. 

I believe there can be great value in paid accountability as it really puts on pressure to perform and can provide you with someone to smack you out of paralysis.

Well one thing that is interesting in regards to Earnest Money is that you take a place like Ohio, I'd imagine it's the same in Oregon but in Ohio the Division of Real Estate regulates the activities of real estate brokerages and their trust accounts but the Division of Insurance is who regulates title companies.