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?

On the other hand, a detailed quote with a higher total may offer more transparency and reduce the risk of surprises as the project progresses.I specialize in consulting services for situations like this, where I help clients evaluate contractor quotes, ensure transparency, and navigate the renovation process with confidence.

With your background in lease management and site selection, that could be a natural next step.Regarding STRs, I can understand the hesitation—accurate expense tracking is critical, and not having that data can make evaluating deals frustrating.

That said it is possible that you need to evaluate your stays and decide if it is worth taking shorter stays or sticking to some longer stays to reduce your time commitment and maximize the revenue for time invested.

One thing in real estate and probably most other businesses is that most people including me don't know how to measure and evaluate risks.  

A couple of tips:Ask specific questions: The more specific your questions (like, “How do you evaluate a potential deal?”

Are you using a 20-35% down payment when evaluating point 3? 

Evaluate Property ConditionOlder Chicago buildings often have charm—but may come with hidden costs.

We had a structural engineer evaluate and he recommended installation of piers to stabilize the foundation.  

I’m currently evaluating whether to go with a Fund Model instead of a traditional JV for an upcoming multifamily project, I will be working as a developer looking to do work with a more experienced developer on a larger scale multi-family opportunity.