Pay the money for a piece of paper or go let my guy take on the project?

For rentals, staying with investments below $1,500 monthly rent is best because tenants who pay $1,500 and up generally do not remain tenants long term. 

I have a long term rental and have a great tenant who pays on time and takes care of the place.

I wouldn't pay them anything upfront...I recommend you always pay for labor AFTER the work is done.

Just keep in mind that less sought-after areas can come with slightly higher risks, but with the cash flow you’re generating, it can still be a good investment.

They always lacked something and I will never have peace of mind. 

The system is what's really broken:1) S8 should have a time limit - get free housing to get your life in order and move on.2) S8 should have strong requirements for taking care of the home taxpayers are paying the rent for. --- We haven't seen a S8 inspection report in over a decade that required a tenant to fix damages they obviously caused.

Now, you need to figure out how to find deals and pay for them.

looking to accurate my rehab costs calculator, specifically in the Pittsburgh area.Of course, It varies from one investor to another, depending on the quality, standard, size, condition, and team.I am looking to get a range or see how much you pay for each remodeling. 1) what's your range for remodeling a kitchen completely (granit, backsplash, tiles, etc)?

It’s great to hear how the community has supported your success with Airbnb, and it's awesome that you're now paying it forward by helping others achieve their goals.Your experience with short-term rentals and as a newly licensed broker will be valuable to so many.