My purpose behind my decision to pursue REI is to gain financial freedom for wife and I, my future family as well as have the ability to make sure my parents are well taken care of once they reach the retirement age.If I had to label myself I’d want to be known as an open minded rental investor for all long term, mid term and short term investing, with the occasional flip for quicker capitol to put back into another rental.

And keep in mind that the rate on the 2nd lien will likely be 10-12% so depending on the cash flow it might not actually yield that much cash to you at closingMore importantly, it's just more debt so ultimately it sounds like you need an income-producing event to actually improve your situation and avoid some of the consequences that you mentioned

Not sure when you purchased the property, but keep in mind conventional loans require 12 months of seasoning before you can use the appraised value for a cash out refi.

My work is located in Louisville, Kentucky but I don't mind driving 20-30 or a little more.

Read The Hands-Off Investor.Important to keep in mind here in late 2024:  The market has been in a down cycle for the last three years. 

Most developers look at a piece of land and have a "end goal" in mind and work backwards from there.

Will definitely look at your post and thank you so much for offering your help I will keep that in mind. 

You should check if the bank feeds work with your bank otherwise, it's a deal breaker unless you don't mind manually doing the data entry.

This is something I will have to keep in mind for myself in the future.

Keep in mind your other associated costs with being an agent.