If you're looking for a 3/2 Tudor, you can quickly eliminate the 2bed/1bath trailer house or the fourplex next to the strip club or the commercial mechanic shop.

Background info: A+ area (wicker park), 3 large 3 bed legal units, 1 non conforming, 5 minute walk to El, quiet desirable tree lined street, huge ceilings, tons of light, original millworkCurrent Rents: $7220 (3x $2000 + $950 accessory unit + 250 garage)Price: Under contract for 1M, expecting about 30k in buyer concessions (nothing major, but seller indicated flexibility to address anything)Pros: 40 year owner, new roof, new windows, new garage, recent boiler/water heater - stout mechanicals, easy to duplex down into basement to make 4bed / 2bath 2250 square foot unitCons: window AC, radiator heating (3 separate meters, but one tied to boiler - owner covers heat), single coin op laundry, porch in usable but older shape, older kitchensComps: $1.15-1.25M for similar but upgraded rental (not condo standard) units.Option A: Do nothing:If I were to do nothing at all and keep rents (below market atm - at 20% down (interest rate is unfortunately very high, but such is the time - 5%) with 4% loaded for fees, $200/month for radiator gas in entire building, it's cash flow $0, CoC $0.Now of course you might be screaming this is a terrible deal - I think there's a lot of value add here for a unique building in a prime area. 

Fast forward a few years, graduated from MIT with a degree in mechanical engineering and now working a 9-5 engineering job which I enjoy but something in me has always wanted to go into Real Estate.Now I am looking for a way in!

I do however see one IOT wifi product that could do mechanical push/pull buttom, there's another window security product (other product) that could also blocking the sliding door to be opened.

(tax accountant with real estate emphasis)

Wyoming doesn't have an income tax.I believe you would pay taxes in Utah, where the property is owned, and I suspect California has a mechanism for taking their pound of flesh.

I have been looking at rental rates on the basis of what my max rate return could be/what type of people are in the area, but I think I have to look at the potential house as a product I am trying to sell with less emphasis on what my opinion on a cities tenants may be.  

@Jinyu Shao when your car breaks down, do you train to be a mechanic?

Multi fam deals have more emphasis on due diligence deadlines which is where renegotiation happens a lot.

I recently graduated with a mechanical engineering degree, and got a job in Michigan.