Instead, she would like me to provide her with combat roach baits.Is this asthma story a viable reason to decline my attempt to immediately resolve this roach issue?  

After going through my own family probate issue I knew that this is what I wanted to do.

My issue is coming up with the 20% down payment may take some time for that next property and I'd rather now wait. 

By having a LO, it reduces the risk the owner will see the success being had with the STR and decide to just do it themselves and I'm out.As for the owner not wanting to be involved with the tax or license issues, that's obvious.

won't allow me to provide specific legal advice in the forum context, I'll be happy to do what I can to give general overviews and talk about some of the issues to be aware of in real estate deals.  

They've been in my SFH rental property for nearly 2 years now (and are staying another 2 years), take fantastic care of the property, NEVER have any issues with them etc. 

The owner also shared that this is an "illegal" duplex but has never had an issue with the city, even when enforcing an eviction.Thanks for any advice on this one!

I have no issue telling the lender.

A housing voucher can only be used to submit a request to live in a property that is located within the geographic authority of the housing office who issued the voucher.  

I always tell clients that if a bank is throwing up a red flag over some issue relevant to you as the investor, or over the deal itself, then there is real risk that should at least give you pause.