For this reason if a new roof is $20k, I need a discount in excess of $20k as I do not work for free (my time is valuable). 

The IRS views this as a part-gift, part-exchange if the values are not equal.If one brother gives up a 50% share worth more than what he receives, the excess value is treated as a gift to the other brother.

Our policy is we only do upgrades with tenant in place necessary to not cause excess damage.  

Get an umbrella policy for $1 million that covers liability in excess I've been a landlord in Milwaukee for 15+ years, I am on the board of the RPAWI and see a lot of legal stuff (like the Koble case at the moment) and as an agent, I've been working with house hacking clients for a decade.

What a Commercial Umbrella Policy Does:Primary Function: Provides financial protection by increasing the dollar amount of liability coverage available to pay for claims of bodily injury or property damage that occur on your rental properties.How it Helps: If a lawsuit judgment or settlement exceeds the liability limits of your underlying landlord insurance policy, the umbrella policy kicks in to cover the excess amount, up to its limit.

As we went, we used the cash flow from the properties as well as excess cash from our employment income to pay down principal.

. $3,800 in labor does sound excessive unless major excavation or line replacement was involved.

ThanksI am not sure what the landlord-tenant code says in FL regarding late fees, but that would be deemed excessive in most states.

Then use the excess proceeds to buy another non owner occupied property. 

.- not allowing command strips fr the walls is excessive.