I personally like the buy-and-hold strategy and we help clients who share this long-term, wealth building mindset. 

There is another house about two blocks over that I have the opportunity to buy off market under market value.

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

What type of properties are you looking to buy?

So, I kept going back and buying things for my girlfriend until he sold it to me.

Duplex can always add additional units via the ADU laws. 8) Related to number 1, purchasing a property with an existing ADU is cheaper than buying a property and adding an ADU.

So if 3 siblings all buy a house together and all live in it when they sell up to $750k can be excluded.If married only one person needs to meet the ownership requirement-but both must meet the use requirement. 

Would also love to connect with experienced Cleveland rental investors.Much Thanks Cleveland is one of the few markets in the USA where buying stuff with the 2% rule is still feasible in 2023.

You want to focus on markets that work with your plan and also where you have a personal connection with someone, even if you build that on the internet.

Quote from @Rachel Vann: Investment Info:Other buy & hold investment.