and would need special permission because her software won’t tell her rates on amounts that small, and sounded like this could be an issue for refinance.

You can’t just rely on automated screenings.  

Nearly 100% of the prospects who approach my firm and DIYed their returns in the prior year are either preparing their returns in a materially incorrect manner or leaving advantageous strategy on the table.DIY software doesn't turn you into a tax professional any more than reading Web MD turns me into a medical professional.That said, if you are just starting out, you can probably get by self-preparing your return until you've reached critical mass and can absorb a rock star tax professional into your budget. 

Hi All,I am currently managing and automating my daily vacation rental tasks through Airtable, which I have connected to a number of online softwares through their API's (Gmail for emails, Twilio for SMS's, Slack for Notifications....etc) in order to achieve my desired custom workflows, and cut down on time spent in front of a computer.I am now at the point of automating my vacation rental bookkeeping tasks and would be grateful for any help with the following:I would like to automatically create a QuickBooks Online Invoice for each customer as soon as they pay for the reservation.

@Zachary Caudill if you can spring for the PM software, a lot of the software like appfolio have a way for tenants to pay in cash at local stores.

@John Underwood I have heard people use property management software or apps to easily manage things and it allows your tenants to log in and pay rent and create maintenance requests.

I'm developing a software-as-a-service offering for real estate investors to find great locations -- down to the block level -- to invest in single family rentals.

@Tom Shallcross - Also made a good point, different PMs specialize in different areas and you need to make sure your PM understands that area and is actively managing properties in that area.I fully believe we are moving towards a very automated real estate space so I'd also look for a PM that understands technology and is adapting and changing as new tech products come out. 

I've never had a problem with guests getting into trouble with the wifi usage.You can control a lot with your router.When I had Satellite internet I flashed my router with custom software so that I could throttle users data after so much usage because I would have someone stay a weekend and use up my while months worth of data.

Here are a couple of areas that tax professionals can and do specialize in:MinistryNot For ProfitMilitary ServiceReal EstateUS Expat issuesResident and Nonresident Aliens in the USOil & GasForeign and Overseas businessDay TradersSmall BusinessConsolidated BusinessesLarge/Multi National BusinessService IndustriesRetail IndustriesManufucturing IndustriesResearch and Development Software Creation and ProductionEach one of these has some very specialized and nuanced tax code that your tax professional should know inside and out.