My long term goal is buy and hold so I have passive income that will allow me to enjoy my family and support somewhat high-end lifestyle.Thank you for your help and input

My plan is to manage those vacation rentals at a 30% cut each, and racking enough luxurious properties under my belt to add another stream of passive income. 

In fact, the tenant does not need to tell you they are using a Section 8 voucher until they submit an application and you are verifying income on your application.If there are other reasons to vacate a tenant, then as long as you provide the appropriate notice and reasons you are fine, such as remodeling units, etc.

I think you’ll enjoy the next steps.

I have enjoyed finding property managers that are more vertically integrated (RE agent, contractor, PM).

I currently work in customer service for a tech company but am considering a career change to being a home appraiser or home inspector.I am in Canada and have looked at the requirements, however I was wondering if there are any appraisers or inspectors in the group who can speak to the actual careers and day to day of the jobs.Do you enjoy the job?

Plus I don't think I would enjoy networking in the least bit. 

I know your tenant has been there for 14 years, but you still want to set aside a portion of your profits for the day when she vacates.

How much more could I get after expenses on short term vacation rentals? 

I see you're from Orlando I just attended a meet up in Los Angeles where a turn key provider with a resort called The Grove was presenting opportunities to purchase some vacation rental condo/ hotel rooms.