Review what is a realistic lifestyle you'd like to have - Buy 2F in high appreciation with great tenants but high purchase price VS 6F in a B- area with high cash flow5.

We are buy and hold investors and have done very well in the transient military lifestyle.

However I believe the market is still decently healthy, just not one you can blindly pick and make wads of money.  

Otherwise, just seeing an HOA with a healthy reserve is a good thing. 

What does it looks like - income, lifestyle, estate transition, etc etc.In general the journey involves several transitions:Risk to securityActive to passive managementSelf control of assets to other control of assetsGrowth to maintenanceEquity to cash flowOwnership to distribution of assetsSo in very general terms the properly crafted exit strategy will have you generating long term asset stabilized passive cash flow in a environment where transition of control is slowly given to those you trust to ensure implementation of your estate plan. 

If you are making a healthy fee, that is not something you should hide from.

I can't stand the W2 lifestyle - like I said I make decent money now, but I can't see myself staying in my current industry for "x" amount of years to save up enough to take the leap into CRE. 

it was very Glenn Garry Glen Ross  a good land man in the day made well over 100k a year even in those years.. they were high flyers and high lifestyles as well. everyone had a jeep wagoner with wood paneling   LOL

This is a lifestyle choice only you have the answer for. 

Your kids lifestyle and future plans without you.