Tenants are entitled to the full use and enjoyment of their housing, which includes having guests visit, so this covers the assistance animals of guests too.

2nd piece is the house hack...We think best course of action would be to have an investor friend we know buy the house in cash, once we are done with renovations, we then take out a full mortgage on the house to cover whatever he paid for it and then pay him back with some interest.

It has a far better chance of being done with proper paperwork and with full seller disclosures. 

@Mike StadelThere's two ways to do it depending on the renovations necessary:- If it's a short term deal, the investors can wire the full amount to the title company, who then cuts any excess checks made out to both parties.- If it's a longer term deal the investors could wire a portion of the capital (enough to acquire) to the title company to acquire the property.

Refinances are a full fresh complete re-underwrite comprising 95% of the same work/paperwork that a purchase mortgage involves, assuming of course the consumer wants the Fannie/Freddie subsidized rates.

That leaves us with you pulling out your money and buying a house in full. 

How quickly will you be able to get past the obligatory learning curve if you jump into real estate investing full time?  

There is also a full 3rd bathroom right next to what will soon be the 3rd bedroom.

I don't know of any insurance company that will compensate you for a bad tenant.Contact the tenant with an itemized list of charges and demand payment in full within 30 days or that they submit a payment plan with the entire amount paid off in 6 - 12 months.

And I haven't managed a full siding project, but 14k sounds a bit steep.