Write out what all he covers and look into subbing any portions of those things out to other sub-contractors.

I am not planning on retiring in my 20's, but I do hope to be able to have a couple rental properties by 27/28 that will cover my monthly expenses so that I can have more time to focus on things that inspire me.I guess it would make sense to maybe try and switch day-jobs while saving and and paying down loans while growing real estate at night.  

I plan on the next investment to cover the increased mortgage payment and would like to continue to use the equity to accumulate more properties.

Are there any things I can counter with or have buyer cover (closing, taxes, fees, etc)?

Are there any things I can counter with or have buyer cover (closing, taxes, fees, etc)?

sarcasm: check the local adverse possesion laws :)Seriously: if it looks like you could strike a deal with him, split or cover the locksmith fee with him to have keys made (by his request).

I sent the $2000 cleanup bill to the tenant for negligence and she is refusing to pay claiming that my homeowners insurance should cover "old pipes." 

If he doesn't want to use debt to leverage his current sum, it's going to be a slower climb, but with less risk (ie if a property he buys with cash sits vacant, he doesn't have mortgage payments to cover).

If it's rotted bad studs can always be sistered on before covering it back up as well.

When i mention we need to come up with special assessment to cover the damages he says he won't pay and other members won't pay either.