You have to overcome objection and do things your not comfortable with to make things work in real estate.

So the general principle for @Matt McGuire of selling one and buying 3 is solid if the actual market bears it out.

Personally, I would keep the 30-year amortization for the flexibility of it, you can always pay down extra principle to pay down the loan sooner.  

Are there any objective measures for how much crime and what type of crime is too much where you would not consider buying?

A break even cash flow deal with 7-10% annual appreciation and your principle reduction each month is a winning deal.

If I read her response and objections and felt that a valid point could be made for her reluctance and continued after I explained the reasons why I want to do the work, then I would leave well enough alone.

It's risk vs reward and opportunity costThink of it this way - each principle payment you make earns (saves) you 10-17%. 

The talking is important, absolutely it matters to understand the client's goals, objectives, etc, but the uploading paperwork is more important. 

The monthly expenses were about $79/month for insurance, $210/month for loan payment ($80 towards principle), plus $40/month storage when I wasn't using it (which doesn't apply for you). 

Originally posted by @Alan Duro:He just desperately wants to make use of this tax loss before he dies (he's in his 70's).I would question why is he so desperate to do so, other than barely on principle "don't want to die with any unopened wine in my cellar."