I was able to make the numbers work by finding multi-units with bonus rooms or sections that I could potentially rent out.

I have some exposure to vacation rentals as my family had owned and managed a few vacation rental condos in the Atlantic City area.I am a Design Engineer working in the aerospace industry and would like to start building some passive income through long term rental cashflow. 

You can use bonus entitlement if you are eligible, without selling or refinancing out of the existing VA loan. 

Lets call that the :( side.2) And there is the happy side... passive income (syndications, passive partnerships ie medical/dentist offices) and passive losses (depreciation, bonus depreciation via cost segregations common in syndications).

Get a ton like tens maybe a hundred million in real estate that you can get bonus depreciation on and that’s very highly leveraged and don’t make to much cashflow or you will pay taxes still so go for expensive appreciating markets.

The remaining $200K becomes additional depreciable basis to you - a nice bonus.

After completing the sale of my full-service restaurant in October and then the sale of my pizzeria last week on 2/3 (just finished training period with the new owner this afternoon), I am officially ready to give my full attention to my RE business.Major bonus points to the restaurant industry for teaching me the importance of knowing EVERY.

If I were you I would make 100% sure I completely understand my exposure before doing anything. 

Bonus Question: what is a good habit for when I go to improve my tax strategy later-on?

Rather, it should be looked at as a bonus!