We tried to minimize risk with renting to high quality military NCO/officer, good property managers, friendly neighbors for eyes on property, maintenance insurance, money in savings, and long term hold for time to gain the equity and have rents rise over time (which haven't actually risen as much as I'd thought).Sorry for the long note, but that is our single family rental  experience as a military member using VA loans from 2002 until now.Cheers!

I was able to go through a little hassle and also about $1000 for an insurance surety bond to get a lost title issued.

They were not obliged to him, he never showed them one house prior (in fact when they walked in to make a contract he wanted to show them other houses), and because he wrote up this contract he wants 20k.

Verification:Rental of Other Property Not Securing the VA Loan Obtain the following: documentation of cash reserves totaling at least 3 months mortgage payments (principal, interest, taxes, and insurance - PITI), and individual income tax returns, signed and dated, plus all applicable schedules for the previous 2 years, which show rental income generated by the property.

Also note that any reimbursement from insurance will affect if you have a loss (or potentially a gain). 

Tenant would like me to use my insurance to pay to have it cleaned up but it didnt hit the home, so my homeowners insurance doesnt come into play.

Plus it would save him money if I paid his taxes, insurance and HOA fees.What would be a good deal to offer him since he has no mortgage and is unmotivated to move in any direction?

Okay i have 2 deals I am looking at for my second investment property both deals are 30 year loan, the mortgage price includes insurance and taxes.. 1)  first deal is 2 houses owned by one person that can be bought in a bundle, both priced at $30,000, they were $34000 and price went down, but the mortgage is calculated on the $34000, its in low income community near 2 colleges in KC, they have tenants in them lease ends in 6 months and have a property manager in place.

Because if I win I can hire the title company for title insurance, or do I have to hire them for initial search to be eligible to get insurance through them?

Because of this my insurance policy cancelled the my plan and after working with multiple insurance brokers I cannot find anyone willing to insure my property.