@Luke H.Hi Luke,  As a private money lender myself I will focus on one element of your deal---5 years is a long time to be finally paid. 

Refinancing isn’t an option yet because of the way we purchased it (unless someone has a bank that will look at the deal differently) our original plan was to pay off our balloon in early 2027 when it is due which the bank will treat as a purchase and then we would wait until we are able to refinance so probably 2028 and then we could pull out a good chunk of equity at that time.

General phone numbers are rarely answered and we are forced to communicate most times via email.The word of the day is patience. 

Realtors typically pre-screen rental clients to make sure their time is not going to be wasted.

Time will tell.

Here was my experience house hacking in my 20's as well: https://www.biggerpockets.com/forums/922/topics/1133476-hous...Cash reserves have saved me multiple times, but my properties were both NOT renovated. 

I believe it is always a good time to invest (sooner the better) and then, there's a better time to invest when all the conditions align, which I missed in 2019.

As I was driving and not doing my daily job, it gave me some time to reflect on how much time I could get back for a seemingly small amount each month.

It's a really sexy application on webinar, but even for the "Get It Now" price may not be worth it if you can't shut it off in a timely manner.  

Build a team with all that time in the morning and and the time you have by walking up early etc.