Having worked for both tech startups and large tech companies, there is a tendency for organizations to focus on one competency, usually the one that the founder has.

In general in single family zoned areas, JADU typically subtract value (I suspect largely due to the OO requirement).

I used $80k to pay off personal debts and $50k to remodel it by myself with my two hands.

I personally haven't done this but I have helped clients do it in the past.Hit me up if you're interested!

It's stronger in court if they do it, nothing personal.

The vast majority of contractors won't want to give bids on properties while under contract unless they have a relationship with that person from prior jobs.

Do large format tile.

Quote from @Sharon Bancroft: @Cameron MarmonI had this same situation and my tax accountant filed the change for me ( one time filling) and we now file it on our personal as a disregarded entity.

It’s a balancing act of controlling costs while also controlling risk of personal injury to your tenants and property visitors as well as maintaining goodwill with all involved at the properties. 

My personal preference for a buy and hold would be an already established area (or an area that's still gentrifying, but has already seen significant progress).