It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

You really need to know your numbers well and build in some good cushion.Tools I use to evaluate rentals and loans.  1.

You need to know how to analyze property and then systematically evaluate property on a daily or weekly basis to stay on top of the market. 

Armed with this information, carefully evaluate whether the numbers meet your investment objectives before making a decision.Good Luck!

I screen individual dogs (of any breed) with an in-person evaluation before accepting their owners as my tenants.  

The problem is that they are not knowledgable enough to understand that the analysis is inaccurate, but start making investment decisions based on the analysis anyway.That is one of the main problems I wanted to solve with DealCheck by providing a tool that takes most of the guess work out of running analysis calculations and evaluating rentals/flips/wholesale deals that will satisfy 80%+ of investors out there.But going further, I think that tools like DealCheck are perfectly viable even for more experienced investors.

That said, the increased rental income typically associated with POHs vs TOHs partially offsets these additional costs, though the long-term financial implications and operational risks tied to POHs require careful evaluation.

These systems are becoming more sophisticated and (my favorite) capable, leading to improved user experiences and potentially freeing up human employees to handle more complex tasks and interactions.

My husband is in the construction business and I am a W2 employee.

Having a rental in the name of an LLC, versus personal name, isn't one of the criteria the IRS uses to evaluate if a property is a rental or not. ...