Should I seek the nicer areas of town to buy single family rentals and keep them above average nice/bordering on really nice....this idea is that I could get better tenants and lowering my pain is of course the goal here.

We also did some white 4 x 4 tile borders when we made the vanity smaller.

Properties that are unique in their neighborhood are notoriously difficult to calculate for accurate investment value.Do you want to be left stranded, committed to buy at a price the Seller already thinks is the best net-price they can get, and you would be gambling it wasn't?

Similarly, if you're the riverboat gambling type, you can try looking into an equity deal where the buyer pays you X% of final sales price and/or a percentage of rental income if buy & hold.

I went through this dance with my cross-border accountant and he insisted that a flow-through limited partnership was the way to go so that is what I am currently using.

The gamble is whether the annual loss on the rental scheme will be mostly covered when I eventually sell the condo.  

What do they care if I buy poorly and lose my shirt down the road.Again, just following what the market and others are doing sounds like gambling , not investing.

I took gamble needing to get  the rent coming in and almost 4 years later they have been the best tenant.

Some of the suburbs of Chicago are particularly high for SFR, while just across the border in NW Indiana taxes are much lower and the environment much friendlier for landlords.  

On top of that you should know exactly who is going to buy or rent it from you and all the terms of the deal.Real estate investment is not gambling.