Other then that I like to cook (I'm a big foodie), I'm also into health and fitness (trying to lose weight), and ideally I'd like to travel abroad one of these days.

This is a statewide requirement, but is handled locally by health departments. https://datcp.wi.gov/Pages/Programs_Services/TouristRoomingH...The city of Milwaukee makes little effort to make it public knowledge that this is required which is why many are under the assumption that there is no licensure whatsoever required in Milwaukee, however that is not true.

Inspect, sure, but free installation inspections is the least the City of Chicago could do after ignoring the health of its residents for so long.

She's in Mexico in ill health with chronic back pain and not reachable, though she does sometimes answer emails. 

I got started about4 years ago but had to step away after some health issues and am just now ready to jump back in!

There will be contracts with the Toledo-Lucas County Health Department for inspections.

Which for many is the only one they get per year or every couple years.My daycare provider's husband is the state inspector that approves and denies STRs out here for the Health Dept. and he said that there has been an explosion of noobs wanting to get in the game, so his denials have gone up quite a bit because they aren't in compliance.

Our trust includes a Pour-Over Will, Abstract of Trust, Asset transfer letters, Durable Power of Attorney, Advanced Health Care Directives, and several other features including specification of the beneficiaries and trustees.

I don't know how the law works in your state, but perhaps similar to Maryland in that if serious repairs (that affect health and safety) are not done by the landlord in a reasonable amount of time, the tenant can file for rent escrow.

To summarize, if the unit does not present health or safety issues, you have 5 years to get it permitted.