I've seen many times landlords try to save a few bucks on the lease and pay thousands in court and eviction fees.

I have sold my primary residence and using cash savings and equity (approx $200k usd) from that to start my investing career here. 

Wouldn't that save me $150x12 = $1800/yr and therefore I could look at my return on that investment as 36% annual return ($1800year/$5000), and therefore this would be a wiser option then focusing on a second property until I remove my PMI?

Here is what I recommend to save yourself a ton of money.Buy 25 blank yellow bandit signs and 30" H-stakes.

I'm retired, the kids are done with college [payments are done] and I'm relocating to Florida to protect my pension.

I provide a bank savings account at a bank nearby the properties for them to deposit their checks/cash/whatever.  

Only about 5 months ago a got a good job instead of part time construction jobs so I'm just now able to start saving money. 

If you close your loan with the title company you used last time, they will probably be able to give you a reissue rate on your title insurance to save you some dollars as well.Good luck

Would the option of using your retirement fund (401k, IRA, ...) as an option for funding a deal be appealing?

Work on getting that credit up, building your savings, looking for a house hack, work in the real estate world, continue to learn and share your successes with your friends.