Screening is very fast and complete - I can elect to accept CC and set the convenience fee (I do charge a tad above costs), and I find its pretty easy to reconcile a tenants payment via "serial number" or transaction ID reported to the bank with both Rentec accounting AND quickbooks - albeit Quickbooks is still manual for me (you can export from Rentec to Quickbooks via CSV... havent got that far along yet.We literally just completed several rehabs (meaning LOTS of expense), so seeing rents come in quickly and accurately is a relief for a change!

It was a complicated and stressful process for me with a huge learning curve.

The compliance coach that was given to me through the company for the 1st LLC I filed with, says that all these documents are important to have in case if I were to get sued, a judge will see that the LLC was operating like a proper LLC, rather than a individual who simply registered a LLC form with the state.   

Keep things simple, do not create any payroll for him and focus on making more money.Now, if he makes $75k net, which is after expenses - then he needs to consider an S-corporation and W2 payroll for himself.Bookkeeping is simple, really: record everything he spends for business in any form that is simple for him: old-fashioned notepad, Excel or Google Sheets if he knows how to use them or apps like Expensify or TaxBot.

If you're operating a short term rental that focuses on <30 day stays, you should consider a Schedule C business.The 2018 Schedule E tax forms has a box for Short Term Rentals but I'm not clear what they have in mind.

The information doesn't even need to be typed in, a person can just click a button and poof, their info is filled into the form. 

However, I have to give some of that up to work in SFR, and that's why I hope to get out of self-managed SFR and transition to other forms of less active investing.

I work in the city and I see that most of the meetups start at 6pm on weekdays, which is a little harder for me to get to.

Being built in 1954 is less of a concern for me than than the quality of the renovation.

@Aditya Maini For me, I wouldn't invest in a rural condo unless my ROI is at least 25% a year, allowing me to recoup my initial investment in less than 5 years on paper.