However, in my particular situation, I am planning on house hacking next year when I decide where I want to live, so this would be kind of a one off before starting a traditional LTR portfolio and this way it would help me narrow down my buy as a beginner whose overwhelmed by options.

Section 8 sounds like a gold mine but it has its challenges that only boots on the ground can really help with. 

This is your property and your investment, not theirs.

Once you’ve identified STR friendly locations, figure out your financing with your brother to help narrow down your price range and market options.

Hey @Stephanie Medina, this comes up fairly regularly and is really an individual situation.

I suppose they would be able to help me figure it out but I’m still trying to determine what is the best way to fund something like this and would it be better to sell off the entire purchase once split into separate parcels or is there a way to structure a deal as to where I could sell off some of the land to repay the loan/investors and also retain a portion of it to develop with my own short term rentals.

If you can DM me, I can get details from you and help you get this funded. 

I am an out of state investor.How have dealt with this issue>Neal Schadler There are multiple property managers in the "build your investing team" section that can help here. 

Did you ever buy this?

I figured I’d share the mess and see what you all have picked up from your own building adventures.So, picture this: a good friend begged us to build them a custom pool house—high-end, fancy, totally outside our Class B wheelhouse.