With the massive increase in STR properties in the US, I am hopeful that lenders and appraisers will evolve to apply income/exp metrics to STR deals specifically, on top of generic property comps.

Typically a few types of PMs out thereThe individual agent, little to no staffThe PM company that's a set it and forget it, glorified rent collectorThe PM company that's a true partnerI would on top of the suggestions abovesearch for a PM that owns their own portfolio tooThey treat your asset like they treat their own portfolio- There should be a full staff and readily available to answer the phone1.

I have nothing to sell and would be happy to help if you think that I can be a resource.

YouTube is also a fantastic resource—it's free and you can learn at your own pace, which is a huge benefit.

The Long-Term Benefits of Working with a BrokerA good mortgage broker isn’t just a one-time resource—they become a valuable partner in your investment journey.

How to Track Regulatory ChangesStaying up-to-date might seem daunting, but the right strategies and resources make it manageable.Key Resources:Local Government Websites: These often publish updates to zoning, rental, and housing codes.Real Estate Associations: Organizations like the National Association of Realtors (NAR) or local landlord associations offer regular updates and seminars.Newsletters and Blogs: Subscribe to reputable legal or real estate blogs for insights into upcoming changes.Professional Advisors: Build relationships with real estate attorneys and property management professionals who can provide guidance tailored to your market.Pro Tip: Set up Google Alerts for terms like “rental law changes” or “landlord regulations” in your area to receive real-time updates.3.

The top areas in value growth are West Town, Logan Square, and Irving Park.

Do you have any books or resources out there that he can dive into to help him hopefully avoids some of the common pitfalls?

Quote from @John Underwood: Gas heat would require constant tank refilling and it would be very bad to run out in the winter.In my experience, if you have  325 or 500 g tank, you can top off in the fall and be good until spring.....Unless I guess you have a big house and are keeping it at 80d.... 

My recommendation would be to get approved as a Landlord, contact the director's office and request that an inspection be completed before a tenant is selected (sometimes they will do this as long as you select a tenant within 14 days - which you want anyways), and have an online application and screening resource in place.