It will never be the perfect and safest time.

Propstream, Batch, and OPENHOUSEit are all great choices/vendors.

It isn't their "choice" to use the Security Deposit to pay rent, unless the lease dictates that.

Is it perfectly okay to utilize this interest and deduct it from my rental income on Schedule E?

If you end up keeping it I would do more work and hire less out because things do not need to be "perfect" for a rental just new and nice.

When an individual property is distressed and hits the market, it's not going to have those instant 12 offers and bid wars flaring up over them that you will see with those purdy perfect white picket fence Hollywood dream homes in areas with optimal school districts for their kids, etc. 

Seeing how you want to make real estate investing your life and career, working as a realtor would be an obvious choice.

@John WiedmanYour first choice should be to find a CPA that specializes in retirement account taxation and one that is local.

Your choice depends on your goals.

Jacksonville not as much as the other cities though and I would call it more like purple, with the red and blue fault lines running within the city itself.Social media is my lead gen of choice for now because it's free (except for what I've paid for BP Premium) and I've depleted just about all reserve capital I had to the point I'm contemplating taking on a day job again (with my tail between my legs having to admit that when I said I was gonna go off and be a hot shot realtor and those corporate psychopaths would never see me again, I was mistaken).