I really wanted to house hack but finding a good deal that allows subletting is pretty much non-existent although I continue to keep my eye out. 

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

I want to keep my current financial position in these properties for tax purposes.

Keep in mind with this investment strategy you are more so running a business than you are investing in real estate.

I’ve done it multiple times and keep getting a different answer ($2500) than the book gives ($500).

In regards to your question about renters insurance I always require tenants to have it and maintain it.As far as your other questions some people go for an LLC to protect their assets (but more work to do tax time to do it right) where others keep it in their name and get landlord insurance and/or umbrella insurance.

I'll try to keep this short, but I wanted to share how I came across a new property that I just signed a contract on.

This is potentially going to be my first deal so I apologies in advance if my info and idea isn't as succinct as it could be.My wife's family is in Louisiana and looking to sell 6 rental homes as they are moving out of town and do not want to keep them as they were self managing.

Wages not keeping up with inflation, so people only have so much $ unless of another government bailout

I think it’s a great career to get into, unfortunately that BS barrier to entry keeps most folks out.