Specifically, you could forego hiring a property manager in the first year, as this is when you would want to apply a cost segregation and accelerate depreciation.

The 2/5 year still applies no matter how long you have owned the house.

Additionally, the right of redemption only applies if the property was owner occupied during the 90 days prior to the sale and this is not the case here. 

But I will say that 1031 will not apply, that needs to be a longer-term hold/investment. 1031 applies to rentals, STRs, MTRs that are held for much longer. 

You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

Last questions, can't a voucher holder apply to any home of any size in their approved area? 

These expenses can create a paper loss, which may offset other passive income or carry forward to future years.If you qualify for Real Estate Professional Status (REPS) or actively manage a Short-Term Rental (STR), the losses can be applied against your active W-2 or business income, reducing your overall tax liability.

@Denise Lang some copy & paste thoughts:TYPES OF RENTAL INVESTMENTSRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

My apartments are in a lower income area, so I don't want it priced too high where it is going to scare them away from applying.

My concern is that if i apply for a HELOC to use for the down payment before i apply for a mortgage, A) I wont get approved due to my DTI ratio, and B) I wont get approved without first showing the bank I have the 20% down payment before pulling the HELOC.