Application / documentationYou will need to submit: a completed STR permit application, letter describing proposed rental use, floor plan, copy of a blank lease agreement, proof of ownership.Fee: The application fee is cited as about $63 for the application / two‐year permit in many guides.Tax obligationsHosts must collect and remit:Florida Sales Tax (6%) on rental stays of six months or less. 

As far as the question regarding the valuation methodology for the practice... typically practices are valued based on a percent of previous years' collections, a multiple of EBITDA or a combo of both. 

I have a tenant who is most often late with rent. She’s asking if she can pay every two weeks when she gets paid. Does anyone have experience with this?

Even if your example has a higher appraisal, you will still struggle to refi out cash because of the rents the property collects.

In particular, I’m interested in advice on:1.Best practices for onboarding new owners and setting clear expectations from day one.2.Effective systems or software recommendations for a solo/startup operation (leasing, maintenance coordination, rent collection, accounting, etc.)3.Strategies for finding and retaining great contractors/vendors.4.Common pitfalls new PMs face in the first 6–12 months.5.Pricing your management services competitively while still being profitable.6.

.: Quote from @Chris Bounds: I feel like people are just trusting it blindly already though, without realizing that it’s just collecting a bunch of info from the internet which may or may not be accurate.  

If that's in the stock market, financial experts say that to be $500/mo.Stock market of course is liquid but I'll keep multiple six figs liquid just for safety.In a recession I'd sleep much better at night collecting monthly rent rather than have terrors about the stock market.

Most S8 tenants have a history of bad decisions, often having convictions, evictions, bankruptcies, chargeoffs, collections, garnishments, etc.

Do you handle maintenance, tenant screening, and rent collection?        

I use RentRedi to collect rent, and ACH payments come with a $1 transaction fee.