She also mentioned a leak in the roof.

I am looking to start my very first rental property in the future, as I go on and learn the aspects of the real estate business.

You now have credit for unexpected expenses that you may not have the cash for such as roof damage, hvac replacement, leaks etc. 

My list includes an electrician, heating & air service, plumbing outfit (though I do most of this myself, I was a plumber in an old life), roofing contractor, and a couple of general handymen.

The roof has seen better days but far from dilapidated and there is a greenhouse area that could probably come down.

With that being said I also start my conversations by explaining the aspects of my situation that make me seem like a credible investor.

A pitch man is going need some really good hype to sell to draw people in, it's most common that these gurus throw out spin on some aspect that is not fully disclosed, like half truths.

Our productivity is through the roof because everything we do is in the cloud and available on the fly. 

Like a good carpet guy, granite, roof, windows. etc. but a good handyman, carpenter or general contractor is tough.My best advice for land lording is 1) screen your tenants very well2) Be fair but Firm. excuses don't count rent must be paid.I have been to Charlie Parish's group.

And you should have an iron clad partnership agreement drafted by an attorney, that details all aspects, like how does a partner get out, what happens if a partner dies, goes bankrupt, goes to jail, gets divorced, etc.