I see many cheap houses in the Sapulpa and Sand Springs area but it looks like the property value is declining in those areas.

Many of the savviest investors sold their holdings just prior to 2008 and then bought back in after the market decline.

Or is it better to just let them answer those questions on the application and decline them if their answers reveal otherwise?

Over the past 12 months, I've noticed a considerable decline in service - most notably billing errors and other confusion with respect to my account.  

I applied for some mortgages recently and was declined based off my schedule E losses last year, one property had large repairs to be done.

Hi Nolan, if I were you I would first ask the seller if they would finance the repairs, but if they decline, I would explore hard money options as well to cover the rehab.

I do understand that one of the most important tips for being a successful investor is having the ability to say "no", even if you want to be the nice guy that everybody likes.2) It might lead to fewer bad vibes between you and the tenant afterwards since it was the big bad owner's decision to decline their request, not yours.

I declined, and instead got a personal umbrella policy in addition to the standard policy.  

When I buy properties, I offer cash, close in 10 days, no contingencies, and 12 hours to accept or decline.

The Chicago area has some obvious issues that I personally think are a bit over stated here on BP (taxes, general population decline), but it is also the third largest MSA in the nation still.