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.

Finally, when you "sell" a house with owner financing, you certainly haven't made an instant $42,500 profit.

These properties are purchased (with the clout of over 100,000 buyers in our group) at substantially under market prices (creating instant equity) in hot baby boomer market areas that are carefully hand picked and determined to still have substantial upside potential over the next several years.

Their E-solutions gives you instant online access to the reports.

My current "cash" situation is still somewhat limited, though I do have a $200k HELOC, and considering applying for a business LOC through the remodel business as well to help add "instant funds" for purchases just not sure how much sense that makes either yet.