Ask your trusted tradespeople (electricians, plumbers, etc.) if they know someone reliable.Local Facebook Groups & Nextdoor – Many handymen rely on word-of-mouth, and these platforms can be great for finding recommendations from landlords and homeowners in your area.Real Estate Investor Groups – Chicago has an active real estate community.

A broker shall not be responsible for supervising, nor shall the licensee be responsible for operating, within the scope of the brokerage or within the requirements of this chapter, activities that would be considered property management, including leasing, maintenance, and repair, so long as the real estate being managed is "individually owned" or "entity-owned" as defined below:(1) "individually owned" real estate is real property in which the licensee holds an ownership interest; and(2) "entity-owned" real estate is real property owned by a corporation, limited liability company, partnership, or trust, within which entity the licensee holds an ownership interest as an owner, trustee, partner, or officer, or in another beneficiary capacity.

Now the island has limited owners to one guest per month.

My last visit was in 2021 and owners were limited to one guest per month.

One CPA is telling us that we need to file a partnership return for all LLCs and the other CPA is telling us that we can place all properties on our Schedule E and use Schedule C for our property management activities We like the Schedule E and C approach because it's cheaper.

That's fewer individuals than active players on NFL rosters.

They are much less restrictive than other municipalities in South Florida that are actively trying to reduce the number of STRs.Let me know if you'd like to talk further on the topic! 

This doesn't necessarily mean just an investor, but somebody who active works in the space and puts in at least 700 hours of work into it per year. 

-- sort of depends where you live and if you want to invest out of state / have the ability to manage a team remotely, the best out of state investors are very active in managing their teams.

Up until November, actively licensed VRD (Vacation Rental Dwellings) could transfer one time to the new owner.