See what you're comfortable with and then you just gotta commit to narrowing yourself to 1 or 2 markets or you'll be in decision paralysis forever!

In the ideal scenario, we picture keeping the property as a cash flowing asset forever and letting our kids deal with it after we die.BUT, if that doesn't happen, and we decide to sell in 7 years or 10 years, I'm going to kick myself for losing out on the capital gains tax exclusion of $500k.  

However, if you are going to be using that space for events, etc. or are leasing it to someone who will be, there could be an impact on your policy. 

Or worse, if the project is losing money, do I get my $100,000 back or it's gone forever? 

We bought a large home on a large lot we thought would be our "forever" home for $460k. 

PG and Baltimore city are notorious for taking forever for an eviction.

- You can get away with doing it yourself forever.

However, we all know that most of these "discount" listing brokerages, or brokerages offering discounted coop fees have houses that are overpriced, usually flipped horribly and sit forever.

You will be in analysis paralysis forever like that.

and my real estate is actually fairly liquid, if i listed at the right price (which I don't intend to, since I plan to hold forever, but if I did) i could sell fairly quickly.