It is challenging in the winter months as people tend to focus on the holidays, shopping, dinners, parties, etc.

Challenges?

I do not know him, but the path he is leading you is a difficult path    Note difficult does not imply impossible; there are people who are successful with S8 housing    In my area s8 is so undesirable that they write laws trying to make it challenging to not allow S8 tenants.  

Removing a lien is challenging because you need the person who placed the lien to sign off to remove it.

I see the price range for these types of properties is between $1 million and $1.6 million, but finding a good deal in this market can be challenging.

I recognize it is a tough RE market with many challenges.  

Challenges?

Thank you very muchJaša This is how traditional banks, private credit funds and anyone in the lending space works.The challenge you will have is finding someone to give you money at X%. 

Rent to close friends and family and on AirBnb to cover my expensesOther than that I think finding a LTR furnished at that price point will be very challenging

And you have to challenge their asking price.