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.

Either way, it's not "easy".The main issue with finding the deal first and raising money later is the consequences of not being able to raise enough money.

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.

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.

The issue I'm running into is that the client has a low credit score (below min FICO guidelines) and with her on the loan, they wouldn't qualify.