I’ve done my research with (reading books, podcasts, etc) but still feel like I’m not doing enough.

Property taxes will likely be reassessed based on the transfer value, so confirm local rules to anticipate potential increases.If you hold the property for at least one year, you can use the equity as collateral for a construction loan, aligning with your long-term financing plans.

Since you know what you need to buy it at and an average rehab cost, I would say $50-70k for a cosmetic flip, set the ARV based on the sample you choose and doing comps and ask them if they would invest in a deal similar to this. 

Quote from @Brandon Croucier: Financing a commercial MF that runs as an STR is possible.Appraising a property based on the income is not, whos to say a buyer would STR the property. 

Do you know an approximation of how much the cost segregation with speed up the depreciation, ie 30% of depreciable base(price minus land)?

I'm sure it was highway robbery - it certainly was based on the man-hours it took - but when you are in a desperate situation, you do what you have to do to get yourself out of it.  

- Each Housing Commission sets their own rent rates, based upon market rents for Class C properties in their area.You should be able to find an online list of S8 rents per bedroom for your area.

I'm looking to purchase my first rental property and have been searching for a deal that would generate positive cash flow based on my projections.

The cash flow that you need to achieve should be based off the rest of your portfolio and your financial situation as a whole.

https://retipster.com/164-arturo-paturzo/Your situation reminds me of this podcast.