Separate the work into 3 separate categories: 1) Those that are specifically related to the future STR usage, 2) Those that benefit you while living in the house and have zero bearing on the future STR, 3) those that benefit both you and the future STR....assign a percentage to the usage.Be specific and complete.

If you want to be a passive investor, you need capital, information and a network, but you don't need specific advantage in real estate.  

Additionally:Is there a specific state where it makes more sense to establish the holding company (now that anonymity in states like WY or DE isn’t the focus)?

The enforcing agency certainly cannot take action against an unpermitted unit without citing a specific health and safety issue to address.  

Here is a link to their zoning district summary:https://planning.baltimorecity...You could also call them if you want more specific information.

I know the IRS asks about entity vs personal members and if they're foreign or not specifically on the 1065 and other tax forms. 

For your specific question about doing a JV on the loan, my suggestion would be that both go on the loan and then do a separate joint venture agreement...because you can not have an LLC on the loan for those loan types, they need to be in your personal names.I am not a lender so maybe one of my lender friends could chime on exactly this would work @Zack Karp, @Michael Facchini, or @Jose Valdovinos?

Then ask them specifically if they help with this sort of thing.Oftentimes owners of businesses want their employees to "think like an owner."

These are not specifically real estate related.

This can range from local real estate clubs all the way up to multifamily specific events such as the National Multi Housing Council’s annual meeting.