However, we were basically gambling on every transaction at this point in our career.

@Steve Vaughan  agreed very slippery slope... we all hear about Hewlit and Packard starting in a garage with 15k of credit cards in the early days... and well look where they ended up.. so who knows.. but it sure is a gamble.

IMHO,  whats important is to walk the property, otherwise, you are taking a vegas gamble with not being able to see the inside. 

Every time a tenant moved out 3 out of 8 evictions or so, it felt like a gamble, with someone leaving the place in ruins. 

my problem is I have not found anyone who will look at the deal until i have it under contract so I dont know how it will go and I am speculating as to what I think it will go for.I don't have 500 or a 1000 to lose on a gamble.

I think it's fine to risk a small portion of your net worth on a gamble, but everything else means betting the farm.Speaking of farm, here are 50 acres in Hilsboro for $3M https://www.zillow.com/homedetails/NW-West-Union-Rd-Hillsbor...Dang, maybe if I..?

Google street and sat view are only your friends to eliminate property....not to determine what you will buy....I swear up and down to people all the time...go look at what you plan to buy.....don't gamble. 

In term of reward, I know the reward of mortgage note, but for tax lien it's kind like semi gambling.

YUP  EXACTLY  its calmed down a bunch but you know a few years ago on BP all you heard was cash flow cash flow cash flow  appreciation is gambling. 

The result is unpredictable: you may still come out ahead due to tax savings, or you may have no significant benefit, or you may lose this gamble.