I am intrigued though and will be checking more out as my time permits.

I have my dwelling contractors liscense & company, so I can pull permits for work that needs to be done.

The economics do not allow for a property renovation, properly permitted and all deferred maintenance issues addressed.  

.* In Some jurisdictions takes even 3 months to just get a demolish permit (even though permit expediter can be used)* Because of these 2 above reasons, I would have to come with high money upfront as I would need to buy the property in cash.

In most cases, they learn of the transaction only when a Certificate of Occupancy (CO) application or a permit is submitted for repairs or inspections. 3.

Make sure it's permitted, warranted, approved by the HOA, and all that other jazz.I wonder how long it will be before the electrical grid collapses.

I would suggest to check with your local laws first.Most likely you will need permit ( I guess you can get away without, obviously not suggesting that :D)) but possible) , also check your zoning.If not possible to create separate unit legally, I suggest not putting an oven in the basement, and rent it without, or live in it yourself

I'll give the county a call to see what they can share on the permit count.

Drop by your municipality's building, permit, and zoning office. 

Now onto the real estate...If you truly want to protect yourself against STR regulations only purchase property with the intent of  operating as an STR where these three principles apply: (1) the use is allowed, (2) the use requirements are protected by in place permitting and licensing and (3) the permissions are transferable through a sale.