I would suggest getting another full-time job for the time being and investing/doing STR on the side until you can fully and comfortably replace the income that you would be receiving from your job.Is your LTR in need of repair?

In the past 10 years, Ocala has greatly improved the employment base, adding tons of logistics and distribution jobs on top of the medical, service and equestrian jobs that we have always had. 

However while people in Windsor doesn't have the luxury of high paying jobs that GTA residents have, is it just a temporary fever of buying houses, or there is really something going on in this city ? 

I appreciate all their training as well.

You can hire a few different virtual assistants on a website such as Upwork.com, train them on how to skip trace, and stick with the one that is the best. 

If I transfer the money to my current job I cant barrow from it.

For what it is worth, as a side note, Youngstown is well known for being one of the most violent cities in the country up until recently, and it was historically mob run, i'm not up on the latest organized crime news and such, but again other than the shut down Chevy Cruise plant IDK what they got up there for jobs...In general when you are dealing with properties in ohio, under 100K you are going to have heavy capex, and generally will be in areas that are challenged and then management will be the make or break factor on the properties.  

Can they be more passive than having a 9-5 job?

We have substantial job opportunities here. 

With a large student population, a growing job market, and people looking for affordable housing, rental demand remains strong.