(We have a pool in our primary only becuase without dogs or kids, rocks or grass both seemed like a waste.)It doesn’t seem to affect insurance quotes at least here.

I am trying to find home insurance but am having a hard time finding one that allows this.Any advice?

You need Liability Insurance and Worker's Comp.

Pretty much the only way to get funds into a retirement account is via earned income.Of course, growing it inside an account is a different issue.With those additional properties you say you are helping your kids buy, are you putting your name on Title? 

As Chris points out, private money is your only option. you cannot get conventional financing because you can't get anyone to issue a title policy on an active foreclosure.

If I bid and win on one of these auctions and there is no other foreclosure pending, do I get Title to the property and then negotiate with the lender to assume the existing mortgage?

At 25% down I’m looking at roughly $2300 for principal, insurance, and taxes per month on a 30 year loan at 7.6%. 

Are they providing a fair service, or do they encourage boosting claims in ways that may inflate the payout beyond what the insured would normally pay (+ the 35% Metro PA would want in markup for their slice)?

two different perspectives but for now I will tell you about the buying side:   1)  You don't vet the seller and property out fully and there are issues - title, financial, etc....

Let's say your taxes are 2k per year and insurance is 1k per year.