Because I’ve been renting to my friends, I did not take the time to adjust the lease contract my dad uses for his rentals to reflect that each tenant is renting one bedroom/bath and sharing common areas (kitchen, living room, dining room, laundry room).

We have lots of aged building stock here - Victorian or older - that can often be found at relatively descent prices due to the fact they are energy pigs.While it is true that a kitchen or bathroom installed today will be a 20yr old kitchen or bath when it comes time to sell, adding insulation, improved electrical, plumbing, ventilation ... all those "under the hood" type of renovations will bring comfort and health benefits to your tenants and operational benefits to your bottom line.

In practice, I have been doing both (1) and (2), and attorney is comfortable with (2), though I know that Bill doesn't like the approach, and he makes some good points.

The only idea I'd have would be to contact the current owner, who may or may not be very excited to discuss the auction where he's going to officially lose his building, but the current owner is actually someone we know, not real well but more like a friend of a friend and I just don't feel comfortable approaching him about this building he's about to lose.

Like most advice I got, if I can generate cash flow or income greater than my current job to help me sustain then I'd feel more comfortable.

I guess the way I look at it as far as going into rougher areas is that if I hire a PM (which I plan on doing) who already manages a ton of properties in the iffy/inner ring suburbs I feel comfortable with it.

You're familiar with and comfortable in an area where a lot of other investors currently don't want to touch.

Since my inspections are tomorrow and I will be spending quite a bit on them, I would like to feel very comfortable with my decision to continue, barring any unforeseen problems with the inspection.

I have purchased property sub 2 but they had equity and I was comfortable doing the deal.

Khakis or slacks will work if you are not comfortable in suits.Make sure you are well prepared and organized with all the necessary forms you might need.