Great stuff @Noe Gil!! 

I would ask them to provide receipts and a detailed letter justifying the 1000 and then have the lawyer draw up the legal stuff.

This village always requires a walk thru by the building dept  (so no doing stuff without a permit) and man was the write up of repairs long.

I’ve seen her stuff on social media so I am tempted to go even though I’m not currently interested in flipping.

Quote from @Lucas Hunt: I see stuff like this fairly frequently and to me it's just a recipe for disaster. 

It takes all of maybe 4 hours a month to keep my stuff in order. 

I would also look at snowballing one property at a time.. get one paid off then the next then the next.. paid off RE is where you want to be if you really plan on using this stuff for retirement cash flow..

Even if he did not use the address as his business address as a roofer he still may/would have this type of materials and trailer needed to do his daily stuff and removing the address as business may not change this fact he would bring home. 

Oh my, all this remote desktop and Windows 10 stuff is so over my head!

Katrina (who owns Dove Realty) and her husband David, who often does handyman stuff are regular people who just do their job.