I feel the market is gambling.

They tend to have affairs and gamble.

And since OP is likely an "insider" under the fraudulent transfer laws, the IRS can likely rescind the sale and also possiby stick OP with a conspiracy to commit tax fraud prosecution (especially, considering, he admitted to it being not above-board here on BP). 

I don't want to gamble that I'll be able to rent it out at the higher rate.Thanks Frankie, At this point I can't tell if there is any value add stuff, because I've only seen the outside which looks alright.

I also gambled on very bad section 8 and lost thousands.

Hello all,I have a prospective tenant applying for a 6 month lease at my 1b1b studio rental unit.  She is an older woman that says she is going through a divorce and wants to move to my town so she can be close to her...

.$10k/year in negative cash flow verses your appreciation....your gamble and your call.

Comparatively, a duplex anywhere near Sydney is around $1,000,000 and rents for around $4,000 per month — no possible way to cash flow so you’d be gambling on appreciation.

I am in full agreement that a positive cash flow is a very important goal, due to the fact it insulates you from gambling on appreciation, equity, and rent increases. 

I took the gamble that possible mold remediation in the basement and structural deficiences wouldn't be a greater than $75k issue.