So, the seller was NOT AT ALL equipped to deal with the difficult tenant situation and the agent wasn't prepared to put a lot of effort into a troublesome deal that was of low value.

Most 5+ units require a commercial appraisal, be prepared for an appraisal investment of $3-4-5k depending on your area and how many units.

I realize this is a huge failure on both of our parts and this would be much simpler if said agreement had been prepared. 

My plan was to take few trips back to Virginia, try to network and prepare my plan before leaving Dubai and going back for good.  

HI Kev, we helped a lot of luxury STR investors this year utilize the accelerated deprecation tax incentive, I would actually suggest checking out the bigger pockets featured tax preparer section and sine it's likely a considerable reduction definitely not try and do it yourself..the investment in high quality reliable tax advice is essential to any investor tool kit. 

When it comes to investing in CA, be prepared for what is coming on the Nov ballot.

I too am in FL albeit the west panhandle, and am preparing to make my first investment deal so kudos for asking a great question!

What’s are some things a newbie investor like me should watch out for or avoid followed by what should we prepare ourselves for? 

I have done some online research but am interested to hear firsthand what things I should be prepared for and probably expect as a new landlord. 

Considering my inexperience in the market driving a lack of capital prepared, I've been looking at the requirements of an FHA loan.