We have not yet felt the financial pain from COVID.

The more you can plan ahead, the more pain you can avoid later.

The city has already signed off on her plans and permit but the contractor we set up for her, and already broke ground, has disappeared.

Has anyone done this and can shed some light on pain points? 

My auto responder sends 10 Q’s. 1/3 fill it out completely, 1/3 disappear, 1/3 partially fill it out.

Construction loans are typically expensive and a real pain in the butt in my personal experience.

I stay away from the national guys because they're kind of a pain, (trust me they try to solicit me for business once a week).

I renovated my primary residence and had an impossible time trying to track down my contractor, who would disappear in the middle of the day, never finish on time, make excuses for everything.

Most attorneys will tell you it is painful to change an LLCs operating agreement once it is created.Creating an LLC is pretty easy. 

Managing other properties can be a pain in the rear with low return.