Improving the gutters I hope would alleviate future settlement issues and most of the cracks except for 2 just look like drywall tape separation.

Talk to your Seller, find out what his concerns are, and get creative finding ways to alleviate his concerns.You're right; it is a hard sell. 

And I keep my properties in good repair to alleviate most of the risk of getting sued in the first place.

What I have learned in the first two years is that background checks, cosigners, and also 3 months deposit would definitely alleviate some of the issues I faced as a new landlord.

I think that's the most important thing you can do, as education helps alleviate fear, so you can be prepared to pull the trigger when the right deal comes along that meets your criteria.

One of the main reasons we are in a partnership is my W2/personal guarantee typically alleviates all of these issues for the bank. 

Paying for a professional house cleaner monthly/quarterly can be a great way to alleviate house tensions about who does the cleaning as well!

@Jim Edelstein investing in a market with a diverse employment base will alleviate some of your concerns.

I wanted to know if I could move the funds (87k) or a portion of those funds into my self guided 401k to help alleviate the tax implications?

In addition, it may alleviate the tenant from calling/coming by at all hours of the day if they think you're the PM and working certain hours vs. the landlord that can be bothered at any time of the day.