There are two aspects to analyzing and buy and hold deal in my humble opinion, and especially a deal involving Multi Family Units. a) The Property Condition and Rehab required:  This is something you should be able to, and probably should do independently. 

Love the aspect of leveraging with debt and being able to refinance the initial capital or part of it back out upon completion and stabilization of the building.

There's also opportunity to move around different groups to learn different aspects of the business. 

As for how hard it is.. that goes without saying there is nothing tougher in the real estate game than this.. simply because you need to be proficient in all aspects  of the transaction.. so I guess you just have to decide which slice of the apple you want and how much capital you have to throw at it .. how much time you have and your sales and closings skills.. which again listening to the guys in the room these were no wallflowers..

This is true for all aspects of REI, either DIY and risk a mistake, or pay someone else to do it more efficiently.

Since you are going to be doing more of a live in flip what are the most important aspects of a home for you?

The challenge with house hacking is weighing the aspect of 'places we'd like to live' with 'places where the numbers make sense.' 

I figure this is likely the commercial space value and I could probably add $50/month on lot rent, or trailer rent on the non month to month trailers (all but one).I'm trying to learn commercial quickly, but I still don't know all the right questions, or what documents to request, or what things I don't know to ask that will bite me (are septic systems legal, violations, etc)I would appreciate any feedback on any aspect of this deal, from my financing assumptions, cap rate, reasons I want to like it, office rental income, etc.The numbers I used are from the P&L they provided, and seem really high. 

I've been looking to master the sub2 method initially until I can move into other aspects of the sale.

I struggled in every aspect of learning wich was expected from a child who was raised In a bad situation mixed with alcoholism and domestic violence, but As i entered my third decade of life the world showed me just how brutal it can be.