I do not have any idea how big your existing contract is and how much may be in dispute, but making sure what your rights and liabilities are now will help you know when to haggle over money and when to write a check and take your losses. 

A Profit and Loss report broken up by Quickbooks class (each property and investment stream is a class)The best thing I ever did was start doing daily accrual-based accounting - for me, having those numbers in front of me and challenging myself to overachieve keeps me focused.I have a vague notion of keeping risk in mind with these things, but I could improve by somehow modeling the amount of risk I'm taking (kinda like alpha in the equity markets).

Unfortunately, unless you are protected by your contract, you may just have to fire him and eat the loss. 

And you will have a more difficult time maintaining it if you fail to visit on a regular basis.Section 8 is not a automatic win (or loss, for that matter) for landlords. 

This gives you a 'depreciation' of $3,636.36 annually, which, when applied to your cashflow, results in a $36 'loss' per year.  

If you overpay, you are going to watch your asset values drop, and they might do so precipitously enough that when it comes time to roll over your debt, you find no takers without putting more equity into the deal to cover the loss. 

The only catch is - the IRA LLC is named as a loss payee / mortgagee on the insurance documents - so I think that could be a red flag in an audit.

Sorry to hear about your losses.  

My DTI is STILL in the high 40's due to the 'loss' of 20% of the income according to the bankers.  

Not to mention "additional insureds" can't collect a check when there is a loss, they only get liability protection (legal defense) in the event of a liability claim.This is an easy fix: You get your insurance broker to issue a policy in your title holding entities name as a named insured and then list the old owners name (the person on the mortgage) as a co-named insured with the acronym "ATIMA" out beside it.