As for house-hacking an existing quad, only putting 5% down in this high interest rate environment will almost certainly mean you won't be "living for free" as is the point of house hacking.

If you are crushing it with smaller deals and find comfort and ease and low ROE (Return on Effort), then stay the course.If you want to scale, you may have to find a partner to help with capital and balance sheet.

Parents recognize this and are comfortable/agree.

Its just so hard in the current environment to get any cash flow with SFR (unless you bought when rates were lower or are doing a well-executed BRRRR). 

If you have experience in managing construction, then you should feel comfortable filing an Owner Builder permit.

Since your experience level (1st investment) is very limited, I'd speak with some title companies to get a feel for comfort level in working with them.You'll be asking a bunch of questions (you should!)

My issue is that I come from a low income background and have fought my *** off, pardon my language to get to where I am now and comfortable.

If you don't mind providing some data for me to reference I'd appreciate it, but understand if you want to keep some or all personal--namely I'd be interested in approximate location, bd/ba count of your property and the rent % increase (or if you're comfortable sharing actual prices) implemented between your last tenant and current one. 

Once you're comfortable with the total gross rent you can charge, multiply the total monthly rental income by .95.

Get out of your comfort zone.