1) I don't foresee prices falling anytime soon leveling out maybe but probably not falling1a) if you plan on living there long term and can afford the payment it probably isn't a huge concern2) Limiting areas limits your options but it is impossible to predict how much an area will appreciate

Other than that predictions of this kind are useless because they are not actionable.

The instrument that protects lender is the mortgage.

The tenant that came with the deal has been at least steady and predictable with the rent.

If there aren't many people interested in the property, a wholesaler would have to consider an offer that has an inspection contingency otherwise they risk holding the property longer than they anticipated.However, if you're in a hot market (and who isn't these days), you may be competing with people who are willing to go after the property so aggressively that they drop all contingencies; this would represent less risk to the wholesaler of the buyer backing out so naturally they would likely choose this offer over yours with contingencies.If you're finding that all deals you're coming across do not allow contingencies, it may be valuable to spend some time learning how to expertly predict repair costs on your own so you can determine if a deal is a good one without paying for inspections before getting it under contract. 

@Scott Stover, if you are in it for long term (10 years+) then  go for it, but be mindful that the bay area housing is at it's peak - lot of BPers are predicting/hoping a bay area housing market correction for far too long now.

And services have been cut to the bone.At some point we likely see bankruptcy (as predicted by the bonds), but even if we dont, its fair to say Illinois is not a growth state, and that costs for fees, and property taxes are likely headed up.So declining population, radical tenant friendly laws and high government costs all point to me as a place I would not want to invest.

This helps me as an investor and as a realtor, because I can more accurately predict expenses on small multifamily properties or larger apartment buildings in my target area (Berwyn/Brookfield). 

I would predict that the areas with smaller units (1-2 bedrooms) would cater more to young professionals the most.

Real estate is, in my opinion; more logical, predictable and all around fun than the stock market...IF you buy right.