As a property manager, when I am asked these questions by a potential owner here is what I say:A good property manager will ensure the property condition is maintained (actually make visits or have visits performed).  

The tenant originally stated he had gambling issues and today when he called he said he had money invested in the USA stock market which 'is taking a long time to clear' this seems like an unlikely story and another ploy to extend the eviction process.

Not only does the mortgage require that I maintain adequate insurance, but for my own sanity I wish to have adequate insurance. 

Try to maintain control of everything yourself.  

You also should interview the owners and find out how much it costs to maintain it? 

See following for a list of lenders. https://www.biggerpockets.com/blogs/3441/51027-nonrecourse-loan-debt-for-self-directed-solo-401k-investmentAnd following are the similarities and differences between the solo 401k and the self-directed IRA.The Self-Directed IRA and Solo 401k Similarities Both were created by congress for individuals to save for retirement;Both may be invested in alternative investments such as real estate, precious metals tax liens, promissory notes, private company shares, and stocks and mutual funds, to name a few;Both allow for Roth contributions;Both are subject to prohibited transaction rules;Both are subject to federal taxes at time of distribution;Both allow for checkbook control for placing alternative investments;Both may be invested in annuities;Both are protected from creditors;Both allow for nondeductible contributions;Both are prohibited from investing in assets listed under I.R.C. 408(m); andNeither may be invested in your own business. 

There's a level of control of your own destiny, whereas if you're buying stocks you don't have much control over what a particular company does.

You can use a VA loan as many times as you'd like, as long as you maintain entitlement. 

A service contract may be the way to go.You let your tenants know ahead of time your coming out for inspection of unit and you maintain your building, the best you can.

Ideally I would like to go ahead and get it under contract and sell it to an investor with a provision in the contract that the owner maintains possession of the property until a specific date.