You'll need to be able to substantiate your status if you're ever questioned about it, but it sounds like you're really good at record-keeping already, so that shouldn't be an issue.

Make sure you have capital to weather any issues and to take advantage of any great opportunities that move you closer to your goals.   

The issue i face is that the only access to my site now is through an easement from a busy shopping center.

I'm not a huge fan of out of state investing and I have 3 properties in Indiana, too many issues with being 2000 miles away.Also no one has brought this up but you said you moved in with your bf.

That may also help put your mind at ease or alert you to a possible issue. 

Unless you have 10 properties going at once, you can manually update these without much issue.

or maybe I can pull money out of first property to use as down payment on next one. but then I still can't technically pay all cash for either property unless use hard money / private lender.  

My primary issue is the value added by the ADU versus the cost.  

We are not able to make repairs as needed due to these multiple issues.

We just don't want our clients to face issues if they were ever audited and I'm giving you the same advice!