The one thing to consider is that IL and NY are both not landlord friendly states.

:) Would love to make some connections/friends here! 

Finding an investor-friendly agent is key and they should be able to help you with 1-4, I'd say talking about those questions you asked would be the perfect thing to ask any potential agents you interview! 

Hey @Aaron Price, I think the best way you can get started in real estate is to reach out to local investor-friendly agents in your market.

Just basic face to face talks with people soon to be friends.

In my market, which is a fairly economical place to build, I am friends with full time builders that are in their properties about $150k/door for construction level finishes.  

Especially in a high interest rate environment where cash flows on long term rentals are muted and there is significant capital required to purchase and list on airbnb.I live near NYC but would invest out of state in an airbnb / landlord friendly state.

My investor friends who joined an investing franchise were severely disappointed.

Hey Christine, I might be biased, but you could look into Cleveland, Oh.Here are a few things to consider against investing there:- Slower appreciation compared to some other markets- Harsh winters, which can lead to higher maintenance costs- Many discounted single and duplex might need repairs or updates, especially if the previous owners haven’t kept up with maintenance over the years- Some local regulations to be aware of (nothing crazy, but worth noting when trying to close deals).But there are also some solid reasons to invest in Cleveland:- Affordable properties in the $100K-$300K range- Strong long term rental market due to a high rent to price ratio- Landlord friendly laws overall- Potential for great cash flow- Opportunities for Section 8 tenants- stable market once you have the right team in placeEvery market has pros and cons so it comes down to your budget, risk tolerance, and finding a reliable crew you can trust.

A friend in Austin recently added a photo of their library wall, and suddenly they started attracting more “workcation” bookkings.Tailor Your Alt Text to TravelersAirbnb’s AI doesn’t just categorize listings - it also matches them with guest search intent.