Generation Skipping Trust (for grand kids) and another trust that kicks in on first to die.

One more link probably won't matter on the price, if someone wants a grand, just lower the offer and let WF take the hit!

You can't flip for a couple grand to have it fixed and then you lose your tenant...and they have right to break the lease and move out!

However, I'd recommend at least five grand, preferably ten, as a reserve. 

You could pick up a few grand in finders fee which would be a significantly higher and less risk return than the example above2) Find something like the deal above you proposed and sell that package as a cash flow opportunity to an investor.

And on Chicago power outs, keep investigating, but my favorite brand (and the one in my master plumber's crawl space) is a Zoeller like this (600 bucks for model with battery, which I don't have) so three grand to hook it to a piece of pipe seems high, but maybe your plumber has a higher end, higher capacity pump...

The grand irony of it all is that you sir live in one of the few markets that is more profitable over the long term than mine, and if you had just stayed local all those 13 years and advised your clients to do the same, your returns would have completely smoked what they are today ... of course, I'm sure you will agree to disagree on that too as it doesn't help support your business model.

Seems like in the grand scheme 10k for the damages is not that big a deal.

So, without a record, and tapped out of cash, I am boned for another few years until I can save up a fresh twenty or thirty grand?

A whole lot of setting the stage to steering you to their Hard Money and Private lenders (Grand Coast Capital) and even their rental property investment division Passive Income Club.3.