I’ve been addicted to DIY home flips for years.

Make a simple spreadsheet or written list with the features of each and see which ones appeal to you most.

Instead I will offer a simple suggestion.  

"Keep it simple, stupid."

I did have a (hopefully simple) question though in hopes of some guidance.

It's honestly that simple, all boils back to this simple fundamental.

You may think you are saving money, but your attempt to evict could be thwarted by one simple mistake in the process, the tenant could get the right to stay longer, and you'll have to start the process all over again.The tenant acts like nothing is happening because nothing is happening.

I am sure plenty have tried to DIY it 

@Dakota Timm need a contractor assessment but you are talking in the thousands and simple to impossible. 

I've purchased and sold many properties this way and feel it's a wonderful tool, but with risks.In the most simple form, you sell the house to your tenant and get a note in return.