I've dwelled on the idea of just going self-employed in a small window tinting business but am worried that would make it difficult when it comes time to sell my house and re-invest in some bigger property especially since I won't have at least 2 years of tax documents for the business.

I don't know if its a statewide thing, but I know at least some areas are subject to them currently.Here in the 'Armpit State', there's similar law for 3+ units (Multifamily and Hotel Dwelling Act - or something like that).

I live in Chicago, and being a city guy I am interested in starting out by investing in smaller multi family dwellings (2, 3, 4 flats) doing minor rehab/repair work, maximizing rent potential, minimizing maintenance costs by managing the buildings and tenants myself, and holding on to them for a while and see what I can make of it.

I don't know your area, or legalities with basement dwelling, so I can't comment on that any further than, is it legal, is it permitted?

Also, my experience as an investor is that, even after a larger deductible, I have the resources and experience to get repairs done more efficiently than the typical homeowner which mitigates the impact of the larger deductible somewhat and makes the up front premium savings more attractive.Regarding personal property, things like kitchen cabinets and the HVAC system should be covered by your dwelling policy.

Trade those duplexes for apartment buildings and buy businesses.It has taken me awhile to feel comfortable buying single family dwellings for rentals.

I started thinking about what am I doing this for and why am I doing this again and how much work I was going to have to do over the next two weeks.So all this stuff was rolling around in my head and I'm driving home from work with nothing on the radio (I usually have a REI podcast or audio book in) just thinking about all that's going to happen and I start dwelling on the what-ifs then it dawns on me as I'm driving down the road that that number on the bottom of the statement is smaller than what most people spend on a car.

In Minneapolis for example, in properties that are zoned R2B, only 5 unrelated persons can occupy each dwelling unit.I rarely see rooms for rent anymore (boarding houses).

For some of my bigger projects I'll trudge through the calls and empty promises of out of state investors, but for my single family and smaller multi-dwelling wholesale deals its just not worth the hassle for me.

John gives good advice.When planning any building like this, check with the local planning and development commission to make sure this is doable before you spend any more time or resources on it.Here in seattle all single family lots allows a second accessory dwelling, sometimes called a mother-in-law.