Did you buy using a 1031?  

You’re shoveling snow with a shovel; they are using a snow plow.  

This phrase would concern me, outside of just using a form agreement - "in order to grow as quickly as possible."

My question is, when is it the right time to start using a property management software and which one would work best for my current situation.

If you are leaning towards using a property manager or think you may at some point, just make sure you budget for that in your analysis so that your cash flow figures are taking that potential expense into account.Since this would only be your first property, I don't think you need a professional hiring firm--it would probably be more beneficial for you to do the interviewing yourself to be sure that you set expectations properly, are aligned, and can work well together.

I bought a wholesale property last January using a hard money loan with 80k in renovations.

So, your portfolio will actually be sucking cash out of your life, if you buy a traditional long-term rental using a HELOC as your down payment, for many years. 

Thanks I have originate many of these AIO loans for almost a decade so I am familiar with the products, the pros, the cons (nothing is perfect), the qualfications needed, how to utilize them, etc.I dont use the AIO personally however Implement a similar strategy manually using a commercial line of credit which is similar in that its based on daily interest (Rate/365Xdaily balance = daily interest cost).

The main differences I can spot are the fact you will have 5 separate tax parcels/ID’s to pay and you will finance the property using a blanket mortgage.

This lets you claim the previously missed depreciation all at once on your current return, using a Section 481(a) adjustment.