Househacking can be a little complex for tax purposes.You have a primary residence in addition to a rental property.You are eligible to deduct direct and indirect expenses related to your rental property.Direct expenses can be considered items like repairing an appliance in the rental unit  or doing the flooring in the rental unit.Indirect expenses are items are items for the full house that you would pro-rate to your personal residence and your rental property.

Many times borrowers overestimate how much the property will be worth after their repairs.

Honestly, it's too bad that the operating part of your dad's business does not carry with it some residual value of some sort with regards to that commanding a sale price.My hunch would be that this would be far too risky to embark on as a first go of things.Especially, from what you're mentioning this may have a large impact on the quality of your dad's retirement.If you have the funds and can structure something, the place to start would be to engage with an A/E firm to get a cost estimate generated for a concept building like you're mentioning. 

Limited is a max of 35k in repairs, nothing structural is allowed to be done (you can replace the roof put in a new kitchen, but you cant repair a foundation or cut a hole for a new window for example).   

Is that cost so high because it includes significant structural (such as moving posts) or repairing foundations or lowering slabs?

I'm looking for a software where I can track data inputs like who was late, how often they were late, repair costs by building and overall YOY/MOM, etc...It would be amazing if I could create my own dashboards.

@Loubert Antoine My plan is to basically fixed the side I’m going to rent out first and live the other side for a year while I repair it, then move out and have rent that side out.

I have had great results from using these sources and get tenants who pay on time, keep the property clean and report needed repairs responsibly.   

Serve them notice, evict them and move on.Your life will get really easy when you have quality tenants that pay on time. 

In your description of the deal, I didn't see what repairs you plan to make or your estimated budget and timeframe.