Also the landlord rules and regulations are not in your favor in Chicago.

Also banks tend to look more favorably on those owner occupied 4-8 units.  

However, that seems to exclude reinvesting in your business, which I know Kiyosaki is in favor of.So my question, for those of you that have made this transition, is did you target your monthly expenses as your transition point?

Mess around with short term rentals or trying to get higher rent to fix your cash flow, and hope appreciation works in your favor.

If it's a bad time then please tell me to hold off until the market is more favorable.

However, purchasing property is a business - not a financial favor.

Matters were corrected in my favor and closing happened the following week.

That argument usually is used when a property manager is involved to prevent the tenants from going around the property manager and seeking special favor from you. 4.

Improvement costs won't increase a whole lot considering I called up some favors. 

It looks like housing prices are more favorable for investing in the outer areas like Winchester vs. parts of NOVA closer to Washington DC.