How would you recommend, or what resources would you refer for us to properly figure out how we spend our time and appropriately get compensated for it?

Having a mortgage and your normal STR insurance is already 2 levels of protection. 

Rather than paying for childcare services from a large organization, we found that it was significantly cheaper to pay for a second mortgage than to pay for childcare.

In our case this was an annex built without proper permission, which limited the m2 that the bank would value the property against, and limited to how much space we would be legally allowed to use.

I really believe in my hometown and have a good grasp on it so up until now- I have simple bought whatever I could as soon as the bank would give me a mortgage.

The strategy I'm following for my first house hack is to acquire a multifamily property (duplex, triplex, quadplex) or SFH w/ an ADU (or potential for an ADU) as I am mainly looking to simultaneously acquire my first property and subsidize my mortgage payment.

Both hold their own mortgages which is very convenient as well. 

If things get tricky, consulting a local attorney experienced in landlord-tenant issues can help you handle the situation properly.

I'd have to see your overall layouts but I think you are on the right track. we build 3 story stacked triplexes and it's very efficient so don't be afraid to go up either. anytime you build more than 1 structure costs are much higher but if its just to offset mortgage and you want to be separate then I understand. 

Specifically, under a properly structured Trust the following limitations will apply during the period that the property is held by the Trust: (i) the Trust cannot raise new capital; (ii) other than in the case of a tenant bankruptcy or insolvency, the Trust cannot renegotiate or modify an existing loan nor can the Trust refinance or enter into a new loan during the period that the property is held by the Trust; (iii) the Trust cannot renegotiate or modify its existing leases or enter into new leases other than in the case of a tenant bankruptcy or insolvency (in the case of a Trust that adopted a master lease structure, this limitation applies to the master lease and not the underlying third-party leases); (iv) the Trust cannot reinvest the proceeds from the sale of the property; (v) the Trust cannot modify or improve the property other than undertaking normal maintenance or minor non-structural repairs; (vi) the Trust cannot hold its reserves other than in cash or short-term obligations; and (viii) the Trust must distribute all of its cash, other than cash held for normal reserves, on a current basis.