I, along with all other owners, once had to pay a special assessment of $33k for dry rot work on the exteriors of all the units.Like the previous person stated, it's possible they don't have the funds or are being frugal which is good.

When notified the selling agent said he will put down some quick dry and a bucket, but I believe this needs to be monitored more closely if it is not properly fixed. 

Some cheaper companies will still use the felt paper, but there are much better products available nowadays...that old felt paper will dry up after a decade and be basically worthless.

The government handout money has made its way through the system now and the consumer is drying up.

Is the land high and dry?

If we lose that because my brother moves in upstairs and they stop paying, we'll be underwater when savings runs dry.

This would give them some skin in the game and would lower your outlay. 

I understand that having confidence is key and that I have to have thick skin to persevere through all the no's and going for a period of time without getting paidbut I know I can do it.

His main concern with having no "skin in the game" is if I fail to perform and don't pay him for up to 6 months before a hypothetical foreclosure or him taking the property back. 

What about hosing off the driveway after the hunters skin and butcher deer?