Owner occuppied loans regualted in every state .. must have state license and NMLS registration.NON owner occ loans on 1 to 4 units are regulated same way in about 15 statesin the other states they are unregulated.Keep in mind though investor loans do not follow the same rules as owner occ and rates can change charges can change closing dates can be blown through etc

Insurance was really created for catastrophic events (fire, flood, etc) not for small claims.

Beyond property owner losses are retailers, grocery workers, dog walkers and all walks of life whom’s livelihood was interrupted.

For example, they won't need to cover your personal belongings (furniture, clothing, etc.) because you won't be living there.A landlord policy should cost about the same as a homeowner's policy; it just changes what is covered.

The market in the area is dynamic and continually changing.

I think initially it makes sense to find properties that already have finished basements, in-law suites, etc. as converting those spaces to ADUs will be inexpensive and create a significant amount of rental income ($2,000/month+ in most areas close to the city).

Considering the change as the STR numbers just aren't working, especially with the associated expenses and turnover frequency.

I am a little late to the game and have been told several times throughout my adult life to invest in real estate, but I ignored the advice.

However, if your time is limited or you don’t want to deal with tenants directly, hiring a property manager can make your life much easier—just be sure to choose one with solid local experience.Are you currently house hacking in Chicago?

So, overall, I think these four areas are very distinct in the style of life they offer.