How do you recommend that someone like myself, and others seeking private money lenders, prepare ourselves in order to be an educator, advocate, and partner (not in the legal definition of joint ownership but in the non adversarial perspective of wanting to be helpful) for our current and future lenders so that the situation is a win-win for everyone involved? 

If there is a right method I most certainly have not found it yet- but I am sticking to my buying criteria and making sure not to waver from my perspective of what makes a "good deal".

By definition a cabin is a small woodland retreat, but I guess it is perspective. 

I don’t know where you are located, but maybe this will help give some perspective.

From a lender perspective they have their minimum DSCR that they are comfortable with lending and qualifying the loan for.

Hope this helps and feel free to reach out if you and your husband ever want to talk real estate investing as we clearly have similar goals/interests, always fun to chat about REI and just get to learn from other's perspectives.

I own 21 units in the area and I am an agent so I can assist from any perspective.

If that isn't the issue, odds are you are making things too cumbersome and involved for the perspective tenants to want to deal with.

The increase in earnest money after lender work-orders is strange... it sounds like you've got some good perspective on the experience, and plumbers are generally cheaper than lawyers.

That usually helps out into perspective that my time is valuable, and Im not just going to waste it.