If you know how to predict those - teach me.But if you do flipping, the resulting income will be counted for the taxation of SS benefits, no matter how you structure it.

Yes appreciation isn’t predictable.

Unfortunately once lost you can not predict when you may have to sell and therefor a definite risk of loss exists.

Sometimes the foreclosure process can be a little predictable but if you've got a good team monitoring your timelines you'll be fine.I'll reach out privately to put a paper in your hand that lays out a good road map of the 1031 process.

However, if recent presidential elections are any indicator, don't put too much stock into early predictions.

Then all your friends should be able to become billionaires when they actually predict the crash. 

Macro economic predictions are too un-knowable. 

Since we often talk about owning real estate for multiple decades, it is relatively safe to say that the end price will likely be relatively close to it's predicted value.  

AirDNA and other sites are not going to be able predict what kind of an STR host you are going to be, what kind of exact experience or amenities you are going to provide, all of which dictate your reviews and consequently your booking performance. 

Groundfloor recently posted an empirical analysis of estimated ARV for all loans that subsequently repaid in 2018.The data shows that the median predicted value was 4.7% lower than the sales price, while the median appraisal value was 8.6% lower.