Hey @Rene HosmanAs a NYC broker, I can tell you that zoning knowledge is absolutely crucial for spotting opportunities, especially in urban markets. 

Hi there,Given the complexity of your situation—owning a rental property in Florida while residing in Illinois, house hacking with your daughter, and planning to claim tax breaks—it might be a good idea to consult with a Certified Public Accountant (CPA) or an Enrolled Agent (EA) who specializes in real estate taxation.While your current tax professional at HR Block has experience with multiple properties, a specialist can offer more in-depth knowledge on multi-state tax issues, rental income reporting, depreciation, and maximizing deductions specific to real estate investments.

So, be prepared to learn a LOT or to hire or partner with people who have the knowledge and experience in these other areas.

When you have control of your budget, money saved, and enough knowledge to be dangerous, take action!

Check the in person events and meetups in your local area, our online community is full of knowledge and folks willing to share and still nothing replaces the opportunity to interact IRL, you never know who you will meet and where that can take you on your REI journey. 

Is it just based off knowledge from experience/visiting with boots on the ground/from speaking with other investors/realtors?

There is a plethora of knowledge here and some great resources. 

Lots of good knowledgeable folks on here, and good local PDX/VAN people as well.

What signs or knowledge can help someone feel confident at the very beginning?

The second categories are techniques and strategies than CAN and DO work, but the students of the mentor just don’t have the experience, education, knowledge or skill set to make it work for them.