So now I mostly hold SPY and "gamble" on some individual stocks.

You never know, but with the info you told me it feels like less of a gamble.

Also on another topic, i highly doubt the homestead exemption is the same set of rules in 1 year.All that being said, to be clear, you think that taking roughly $130k now would be better than gambling that in 20 years, i could take $700k?

If their is no cash flow then you are just gambling and it’s all just wishful thinking of the uncertainty of the future.

I do understand that there is a lot to be done in the area but there is a revitalization plan for that particular area so I am taking a gamble on it!

(yes appreciation, but thats IMO gambling)2. good property manager solves everything3. do your own research.feel free to reach out

Would have chosen the HELOC all day long if our property wasn't in Texas (Texas limits HELOCs). 

I do see the interest with its proximity to Crosstown, but it's a gamble on how long it will take for the surrounding areas to be impacted by that development and you would want to be sure you don't lose money waiting on the appreciation that may or may not happen.

In retrospect, do you wish that you had chosen a simpler project for your first flip (i.e., not a defunct animal shelter)?

I considered using him, but his online presence is really poor, which means unfortunately I'm not going to take a gamble with a huge investment, on him.