For example, for this one, there are 5 4/2 in my area and they have close to the same condition as mine.

And What other conditions/terms/costs do you calculate when underwriting the potential of a deal?

Even a single family builds can vary significantly based on site conditions and required structure/design.

Quote from @Daniel Tanasa: Another option is to get a small cash out refinance from the house you plan on fixing up, if is in financeable condition, and use that to fix it up, while still cash flowing.

Are there additional conditions or taxes to consider when purchasing in these regions?

, see that under "sale conditions" it's listed as 1031 Exchange, what affect would that have on me - somebody interested in purchasing their property?

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. 

While algorithms can analyze data at scale, real estate isn’t just about numbers—it’s about nuances and the most important component of real estate is understanding its value, and that to me (maybe I am old school) but can only be done by physically visiting and walking the property.So for me, factors like local market conditions, property inspections, and borrower credibility can’t be fully captured in a formula.

The home was clean and in great condition.

However, it's a deal in a different state and during the Facetime showing, I could tell the tenants were gross and makes me think they don't care about taking care of the place or their living conditions.