Short answer is yes it can be done, it is just more complicated and your finances/credit have to be very good.

Their training and their tendency is to complicate matters which, or course, keeps that billing meter churning.

You want an accountant that can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.House hacking will complicate your tax return. 

However, taking out of state trips with them is so complicated and easier said than done.

I just don't recommend starting with the BRRRR method because it is complicated for a beginner.

So, I want to ask: How complicated would you say the actual structural conversion was?

We just got our offer accepted on a house in Centerville with a MIL and I just got off the phone with zoning who told me they are "prohibited, unapproved, but enforced only by complaint" I need to know from people who have this setup in non legal fashion  what complications have arisen, how to prevent complaints and how to find renters if it is not technically legal.

It makes it more complicated as my cabin is east facing so we need a sunny morning when the cabin is clean.I have no open nights in February, but several promising weekday dates in March so I'm confident they will get taken within the next 6 weeks.  

The finance part is a bit complicated for me.

Hi guys!So I'm a resident physician living in the Bay Area and my fiance owns a 3 BR 2 BA condo in the North Kenwood area in Chicago, a 6 unit multifamily condo building. The HOA was severely mismanaged by a self-mana...