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.

@Scott Simpson, that margin is too tight for me.