The tax value doesn't tell us, or you, what it is actually worth....only market comps, in Similar condition, size, etc. cn tell you that.Hard money, or any other private lender is going to want 20-35% down, and has no interest in making interest for only a month or so.Also generally, the higher you get above the median house price in the area, the longer and harder it is to sell.

Your inspector will look for structural integrity issues, life safety issues/fire hazards and inspect your MEP Systems to make sure Electrical panel, wiring, piping, hot water heater & HVAC systems are acceptable/good working condition.Roof/Crawlspace/Attic InspectionsIf you are afraid of heights and don't want to get on the roof, crawl around in a dirty creepy crawl space or climb around in a haunted attic, an inspector can inspect these areas.  

It's in great condition and mostly up-to-date, but the kitchen is dated ('70s/80s), and it has an attic level that was just begun to be finished and then left off sometime in the '70s or '80s.

Then for $200 cash flow, that is 100% dependent on what price you are paying for the property and what condition it's in.

In terms of adding new pavement, does anyone have real life cost examples they have done? 

To be honest I'd be scared to take on a house in that condition, mostly because I'm inexperienced haha, but I'd like to know how it turns out out for you!

We want to simplify life, not to mention the acreage is worth a good bit but demands little for rent... it's appreciated nicely for us, but in the end of the day I'd like to put that capital to work in the form of more traditional rental homes.

If you are an independent contractor with multiple years operating in your business and reasonable consistency in that income (you don't have one year with $30K and one year with $200K and are trying to claim you make $200K) then you need to keep calling lenders until you get one who can work with you, in my opinion.If my real estate side business and my book royalties from Set for Life (next year) can help me qualify for a loan, in addition to my W2 income, then I don't see why someone with consistent income from self-employment is having trouble -- perhaps the trouble is more in demonstrating consistent income from a sustainable source? 

She may wish to get her life on track some day and decide to settle.

Ideally the property will have one unit that is in livable conditions so I could get that rented out right after purchase and then update the other unit.