I'll use my passive income to supplement me in the early months but will want to get to a point where my passive income goes back into real estate again.

Less if we can make more cash-flow per monthNow, where it can get interesting is any other ways we opt to supplement that income.

In my experience the portable heat pumps do not do as well as ductless in cold weather and I supplement the portable heat pumps with a construction heater in my own home.

I know, very generic advice.More specifically, I would suggest you search through craigslist looking for real estate related jobs.

I use the term "Investment Property Owner" as a generic occupation title.It describes both flipping and rental owner at the same time.

The ad mentions generic house description.  

Speaking as a US urban homeowner, supplementing our retirement income by running 2 Airbnb units in our 2-family home...The "hotel industry" includes a ton of low-paid workers. 

First and foremost, I'll preface this by saying that my current niche is wholesaling residential properties, and that I don't have much experience working with realtors/agents.Anyways, I'm in the beginning stages of building a relationship with a realtor, and they let me know that they know about an apartment building that they are trying to help someone sell without listing it.Being that we know a few people that buy and hold commercial properties, we asked them to go ahead and give us some particulars on the property, so that we can mention it to the investors in our network; for all I know, we could possibly wholesale this property to an investor.Well anyways, they gave us some very generic info on the property (number of units, etc.), and wouldn't give the address of the property, nor would they even tell us which part of town it sits in.

I have being doing it I feel the long way via mutable generic websites but feel like it is very time consuming and must be something out there for exactly this.2) What software programs are people using to manage there business/jobs?

(It's liable to be location specific, so may be best to describe it in generic terms so people can interpret it where it applies.)David J Dachtera"Success is not a destination.