Yes I have been playing around with QBO and finding it overly complicated and tricky to setup for STR..I will keep playing around with it but will also check out some of these other suggestions:) 

You can literally find answers to all of your questions within the confines of this site.

Find local meet ups and find a mentor in your target areas.

You can easily do this on a spreadsheet, and it will take less time to track than finding and learning new software.

For example, not a beach town obviously, but there is Indio, where STRs are very common and if you look hard you may be able to find a deal that could make sense in this market..

Hey Conrad,I would look for another background service as this is an important step in finding a potential tenant.

Owners are supposed to certify to the Board if no sales were generated in any particular month, as well as provide a copy of any Colorado sales tax return or alternatively, a report from AirBnB or VRBO regarding the sales for that month.I find this invasive, crappy, and a whole lot more that shouldn't be said in polite company. 

Turn over is typically higher than a normal rental, so you have to get good at finding and screening tenants/ house mates. 

If you find a bank willing to do a deal like that let me know their contact info.

@Paul Merriwether it's all about finding the right deals.