Now, I have not run out of money yet....I am just trying to get ahead of this before this does happen. 

I visited a friend that lives there in May and it seems like a nice area.

However, I'm currently based in CA, and we pay a pretty penny of our post-tax money to vacation in Airbnbs over the summer so that's one (personal) benefit to purchasing one, and I would like to be able to visit the property relatively easily (ie. by driving there).

We did try to get one group to do it all, but they never got back to us with an estimate after visiting the job site.

How often do you visit your properties?

At the end of the day the goal should be to make enough to give you an optimum lifestyle but not go overboard and cause yourself more work/hassle if you don't actually need the additional income that comes from it.Increasing the quality of the area/properties should make it easier management wise and if you don't necessarily need the cash flow now could end up ahead in overall return compared to the lower end areas, especially if you use leverage.I think it depends on your source of active income as well and how long you want to continue doing that for.

She even says that "this is your 3rd visit and it has not been fixed".

So, if they offer anything of substance I would take the bird in hand and walk away ahead without dealing with any hassles for months.

I would suggest googling (or using Instagram) to find designers in your area that fit your style and visiting their website to see what services they offer.Another avenue is to search for interior design "build recipes" or "design recipes".

My question is: Do I keep the court date and try to get someone to represent me or should I just go ahead and cancel anyways since he has technically left?