On the presumption it is a personal house, I would say to do it as soon as you can afford it, presuming you are looking to stay in the same area you are at for at least several years.  

I also reached out to loanPro.io to see if they had an offering geared towards the person with a single loan that they  need managed.  

People have to take a deep dive into their personal lives why they are not being consistent in their lives.

EXAMPLE: your wasp nestAlso, as you've learned, no one person is consistently going to your property and keeping tabs on it. 

KY seems to be giving out grants for this, but I don't know anyone personally who has done it and didn't know if this was a good route to check into.

I track everything through Monarch personal stuff include because the filters work really good and it gives me a clear financial picture of all my finances as I work towards FI. 

I'd be happy to talk sometime, or depending on where you are at, we could meet up in person.

You also gain access to his Discord group which, to me, is a huge message board that is difficult to keep up with, follow specific conversation, etc... 

Would love to hear more about your personal start/journey in the future if possible.

A good investor friendly lender & agent will certainly help + groups like this and local REIA groups with opportunities to meet in person or on social media and network about off market opportunities too!