UPDATE on this post:I greatly appreciate all the responses, DMs, and advice. 

Hey Ben, we closed about 4 weeks ago- been doing cosmetic updates every weekend since then and should be ready for our first rental in October!

I also use the BIGGERPOCKETS calculators to keep track of things like ROI and cash flow projections and update the data there on my buildings frequently.

"for $___/year, we provide "x" additional inspections")6) Liability policy that covers tenant intentional damage, criminal acts, and unpaid rent when skipped or evicted (through insurance provider that provides this kind of coverage)7) Financial reports per quarter (as whatever period makes sense to you) (this can allow you to advise the owner on the health of their portfolio)8) End-of-year review of the property to show conditions and suggested needed and preventative maintenance items 9) Preferred vendor discounts (requires a contract with a vendor to give better pricing)10) Eviction protection programs (this is usually done "in house" when you have sufficient number of units under your management to be able to offer this kind of program)11) Legal services (requires agreement with landlord attorney to provide those services at set fees)12) Professional photos option (for enhanced listing)13) Professional, licensed home inspection (this is more relevant for older homes to ensure safety and habitability are addressed) 14) HVAC filter replacement program (this can also be a program offered to tenants)15) Pet and ESA screening through pet screening vendor (helps to streamline and increase quality of screening)16) Client portal account for ease of communication, updates, reports, etc.

I'll update here if I find any success.

Your contractor should have at minimum a weekly status update mandatory dictated by them. you need to make sure an in depth scope of work and evaluation is performed especially because you have little experience in evaluating these types of projects.

In Tampa, If it is a nice property in a desirable location with ample amenities it would certainly outperform LTR unless not managed correctly.As far as getting the reservations cancelled from Airbnb - they are being very tough with this recently. 

Update just in case anybody reads this as it might be helpful.

Well done on the update!

I can choose to update the kitchen (an investment) in that property and may not make another update ever.