If not and you're comfortable with the current buyer, you can look into owner financing or the lease with option to purchase route. 

My comfortable price range would be between $500k-$1M.I know that under $1M, you probably won't find something new, climate-controlled, or in great condition, but is it true that there's almost nothing worth looking at in this $500k-$1M range?

Get out of your comfort zone.

You won't succeed in real estate if you don't get outside your comfort zone and just make it happen.Good luck.

Get out of your comfort zone.

Ya went where ya felt comfortable thats all you can do.

While her and her husband relaxed on a beach me and my guy froze our butts of completing the job.

These will help you understand how aggressively you can push for rent increases.For tenants you want to keep, I'd push the rents to an amount that both parties are comfortable with, so they stay in-place and you don't have to spend on turnover and renovations.

We're very comfortable with our purchase even though it's not a cashflowing investment.  

Or let's say he only needs/wants $225k per year to be comfortable - well, he can take the difference and invest in whatever.