I have seen a few people mention that house hacking is possible as well but tricky to find a property that can support that approach.

@Greg Scott thanks for the mention:)@Usman Khan welcome to the "fun" of S8, where you can rarely get ahold of anyone at a Housing Commission office:( THey are all overworked and underpaid.Reference this for your S8 training and maintenance:https://dhcmi.org/sites/default/files/upload/LandlordGuideBo...

As others have mentioned you can do a cost segregation on whatever you'd like. 

(Your income will be $10k higher if you self manage, but as I mentioned before, you earn that $10k by acting as your own PM. 

I notice that you mention two different states when you are talking about house hacking.

Certainly contact the HI and see what he has to say....you may not get far but worth a try.On the other hand, you mention 'exposed wires'....where are they?

-In speaking with investors, others have experienced some of the same issues mentioned throughout. 

I'll add on to what the other Ben said and mention that there are exceptions based on the # of days that you rent out your home to where the income/expenses are excludable (being lesser of 14 days or 10% of total usage if under 140 personal use days).

Santarelli, in two YouTube videos explains the promissory notes investment opportunity (Link), and mentions some of his other ventures including, “cannabis and crypto investing” and producing/co-producing six new Broadway musicals.

I saw one post where someone mentioned using AppFolio’s bulk upload with a custom spreadsheet, but I imagine there are a lot of different ways people do this.I feel like I might be overcomplicating things, so I’d love to hear how others handle it.