I am just trying to educate myself as much as possible so when a good opportunity arrises, I can pull the trigger and feel confident.

Now the city is requesting the following:1) Energy compliance documentation2) Mechanical (HVAC) Drawings3) Plumbing Drawings (Hot, cold water waste and vent. gas)4) Electrical (Complete Drawings)What kinds of people do we need to hire for these drawings and plans? 

Hey all,I am also about to pull the trigger in the Orlando area. 

Through these two events plus and enormous rabbit hole tumble into real estate advise books like the ones on this website (thanks again Brandon) along with an avalanche of YouTube videos and other business self help books like “The 4-Hour Work Week” I’ve developed the confidence and put in place the systems to help pull the trigger on my first two buy and hold rental property deals.

I would just need to update the compliance issues within 90 days.

Now i got those two in line and I'm ready to pull the trigger.   

If you do buy the property personally and then transfer it to your LLC, that could trigger the due on sale clause found in most standard mortgages.

I've been speaking with my CPA (who obviously isn't a lawyer) & my compliance coach from the business who set up my first LLC. 

-Is OP's father willing to go through the compliance hoops of administering a corp for tax purposes?

Boston has apparently had a registry for AirBnB/short-term rental properties in effect since Jan 1st, though compliance is apparently still an ongoing effort.