Consequently, when you get a DPA loan sponsored by the state, you look for expertise, care, and quality from the lender because there is no significant difference in price.

Starting to look for multi-family homes to be able to house hack into investing!

If I were you and could do a refinance and get all or most of my investment out of the property, I would hold on and wait for the market to come back next year.You can get up to 80% LTV on a DSCR Refinance.I assume you are using a Property Manager, I would take a little more control of my future tenants and call their previous landlord to see if they made any repairs to the property while they were there, how many time they were late on their rent, etc. 

I wish VRBO would invest in the user experience of the app to make it more attractive for guests to use it and book with them. 

Not 30 days later or 60 days later when you go find the money or borrow it.Every jurisdiction is a little different as to how things work, but typically you won't be able to borrow your way into tax lien/deed investing unless you are borrowing against other assets you have like life insurance, home equity, 401k, stock margins, or some other hard asset.   

Is the tenant otherwise cooperative and taking care of the place and paying rent timely? 

Hard Money Lending: Hard money lenders are generally comfortable lending to LLCs, especially for investment properties.

I have no idea why he won't just sent the invoices and link since they're easy to take care of.

Should I focus on out-of-state investing?

YES I know there are some that care, but most do not