I think it's unrealistic that I would buy a 100+ unit property for my first GP position.

Hi Jasmine-Congratulations on being ready to turn your primary residence into a rental.Your question is should you use a property manager or self-manage your property.If there is enough positive cashflow or you can afford to pay a property manager, I always recommend doing so for the following reasons:1.

Given your stated position of things, assumptions of skills and network, I'd say your best path is a totally different one. 

Also, to track spending habits - just had a prospect withdraw their application when we asked why they were spending half their income on gambling websites.

You really have a great position here.If your private money runs out or runs tight, then you can explore other funding options like hard money.

And actually being cash positive instead of negative at least your post says your cash negative not making any money so you are eroding your cash by feeding these.. not to mention the incredible risk you take with remote rehab and the time involved ..

If they are CF positive then they will not cohnt against your DTI but will improve it...that's standard conventional guidelines barring a few exceptions.

As others have pointed out, you are actually in a great position!

I was in the position of considering renting to someone with a pittie.  

Since this is a real estate investor oriented website no surprise on the consensus.