I’ve owned a dozen properties for almost 25 years and I’ve spent less than $500 on roofing, and zero on exterior siding/painting.

These individuals have reason to try to sell you services as opposed to actually telling you about the condition of your existing septic.

If it's a vinyl window, or if you could swap out the existing window for a vinyl window without much hassle (e.g. if it's on the first floor and you have easy access to the exterior), then waterproofing the inside shower area around the window would be much easier.  

I'm thinking of hiring virtually from Upwork, Fiver or Onlinejobs as opposed to some of the bigger SEO companies just because of the price difference. 

black top the driveway and trim the existing landscaping and paint the exterior and it will look great 

Dave Ramsey will tell you to accelerate the principal payment and that's not wrong.The opposing view is to defer payments as far into the future as you can.

Buy a cheap house in a tough area, the numbers on paper may look good, but you will have higher operating costs and more headaches (generally speaking) as opposed to buying a solid house in a good area.

. - Purchase Price $38,450-Full Rehab $75k (roof, interior/exterior paint, new kitchen, new bath, new floor, new appliance)- Add full bath $25k (88 sq ft) is the option/decisionAs far as cash flow, here is are the two options....- 3/1 would be...

That would just be a flip to most people on this forum as opposed to a wholesale deal. 

Replacement cost (that day as opposed to last year.), minus amount saved so far, divided by remaining life.