The properties are currently about breaking even based on their first year as rentals, but the management company used seems to be leaving some on the table in my opinion. 

Go with a butcher block island for a dinner table and buy some metal legs from Etsy.

Upsells include concierge services, butlers, parking, local tour guides and activities (affiliate partnerships), renting different parts of your property at the same time to different clients, romance packages, spa packages, up charging for high end amenities, massage/wellness packages and affiliate partnerships. 

Looks like a million bucks and takes just a few hours to do a whole dresser or dining table.

I spoke with my attorney for eviction. but my brother who use to work debt and bill collection told me if this tenant is on social security and works under the table at a job I can't garnish his wages because disability and social security are protected which I find ridiculous since he has been living for free guess these deadbeats know the system so well to get away with things.

Maybe suggest felt pads for furniture legs to reduce noise from moving chairs or tables.

Taking on debt isn't off the table, I'm just really afraid of the risk since I'm not sure how it would impact my current mortgage, or what the worst case scenario would be if things failed.

With a private pool, a private hot tub, and a pool table of their own. 

Install 1x6 lumber over sash building an inner box then fill with blocks, you can build the block unit then install the whole unit, makes it easier to line up your blocks on a table then trying to work in the window.

Fill your vacation rental with an overstuffed couch from '99 and the coffee table from your dorm room.