My goals are to have some STR's in places I'd like to stay at as an option, have the rental income help me reach FI/RE and have multi-family units I could pass on to my 3 children once they are adults.

In addition to the constant tenant turnover, there are the various correspondence/questions and the need to immediately address various issues (the number of less than stellar reviews we have for downed WI-FI is not insignificant). 

I am selling my Manufactured Home that is financed as a Chattel/Home Only, and I have a contract for deed on the land with my Father-in-Law. The land had not been recorded yet, as I’ve been allowed to live on the land...

- The total cost of the re-fi will be about $17k (title, fees, appraisal, buy-down, origination, etc)Here is my bottom line question....should i move forward with the re-finance? 

I believe this company I'm speaking with right now said that they give free Re-fi after this transaction.

I would suggest getting a book like The House Hacking Strategy by Craig Curelop (I'm an agent with The FI Team headed by Craig here in Denver) to help you with that process.As far as managing your own rental, I go through Apartments.com.

Make sure you are very confident in your re-fi ARV and have someone with experience in Baltimore double check the comps you're using to make sure they're valid.

@Trevor F.  I

As long as you’re sure the problems are big enough to risk losing the deal fi you go past your inspection period go for it.

Hope that helps Semper fi