@Jesse Dominguez-Castelan please elaborate:"the house definitely needs some fixes"You mentioned in a comment you did a new roof and siding.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Some section8 vouchers only cover 50% of the rent, while others include 100% + utilities!

No, the topic has been covered ad nauseum.

For instance, your rent may be $1000 per month and section 8 may only cover a portion of the rent, let's say $800.  

There seems to be a glut of STRs in every major market, yet there are RE agents out there telling people that there is demand.There may be demand, but if the owner cannot book their place to cover the costs, how can RE agents be out there telling people that it's a good investment? 

Since you will have what I assume is an atypical unit mix, you will likely need to look at what different unit size buildings are selling for.I.e. 5x 1/1s are $250k/door.  4x 1/1s are $265k/door and 4x 2/2s are $325k/door, you could assume covering to a 4 unit will value the property at around 1.12mm (3x265 + 1x325)vs 5 one beds being worth 1.25mm.  

So I am familiar with soflo.One strategy I am trying to implement is The 4-3-2-1 Strategy:Start with a 4-unit property: Live in one unit, rent out the others to cover your mortgage and expenses.Repeat with 3-unit, 2-unit, and attain your dream home last (1 unit property)After 12 months of living in each property, consider a cash out refinance to use equity for improvements or further investments, if beneficial for you.Build a real estate portfolio of 10 rental units in a 3 year span while generating rental income.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

New roof.