It can be a hard pill to swallow paying 2-3x more than a traditional PM, but the obvious is that there is much more work that goes into operations and you have constant eyes and maintenance on the property.   

Also house hacking can be a great way to cover your mortgage while having someone there to keep an eye on the property when you are gone.

Matted carpet, aged paint, scuffs on tile, etc are all wear and tear in my eyes.  

Facebook can be quite eye opening. 

In my eyes I paid him about 50% of the "proposed work" but only about 30~40% of the work has been completed (mostly demo/frame in).

My question - can I issue a 1099 NEC/MISC to my realtor as a sole proprietor (using my name as Company name ) or do I need to incorporate/form an LLC first?

I am the owner of a small business (LLC- soon to incorporate S-Corp, possibly) and our eldest is heading to college.

Something caught my eye at the end about Landlord Insurance and potentially covering the cost of alternative housing while repairs are completed on the property for a tenant.

While the project is moving along, keep a close eye on the market surrounding it, the list and sale prices for new listings and sales, and visit any that look similar in person.

Value is in the eye of the beholder.