The floor with the two bedrooms is completely outdated (trim, casing, doors from the late 70s) but it very clean and freshly painted.My thoughts are that i HAVE to renovate the bedroom floor: new trim and casing, new interior doors, possibly new carpeting.

He changed out the sprinkler timer, trimmed the large tree, installed crown molding.  

To me, this is investing and you make it work however that ends up, at least when you're starting from nothing that is.So if you have to trim costs, then you can trim them in all sorts of ways and insurance is definitely one of them.

Plan for that.Now start to see where expenses can be trimmed, almost everyone can trim their living expenses some (even $10/week is more than you have in savings currently), and start a real estate investment fund add the 2015 tax refund (note 18 months from now roughly) and you have a start.

We are now left with a leaking shower and no trim due to the water damage in the bath room.

Assuming the cabinets are nice and that these pics aren't making them look better than they are - I would keep the red cabinets and lose the black-and-white floor and trim.  

A lot of times it is easier to pull off the trim, put extenders on the receptacle boxes, and hang 1/4" drywall of spots such as these providing you are not just covering up a problem but rather taking care of a cosmetic issue. 

In new construction you're starting with bare drywall so yes you do have to primer it and then paint everything -- walls, ceilings, and trim. 

If I am walking through a house that I am considering purchasing and the paint job is sloppy, the doors rub in the frames, the windows are hard to open, and the trim and drywall aren't properly prepped.  

Also, with the difference in thickness between panel and drywall, trim, baseboard cuts, heating/cooling vents, etc. may need to be readjusted or replaced as well.