The problem I'm facing though is that the other homes in the neighborhood have renovated kitchens (probably less expensive than the roof) and are older too.  

They are offered on a first come first served basis for the face amount of the lien.

Now this is the nitty gritty that "real estate investing" is really all about.This is the bottom up.All these paper pushers wondering why their profits aren't higher is because they don't know everything bare-bones like this.

I'm in cheaper NH and 15K is just barely enough to do everything yourself with a fourplex, leaves nothing left over for anything unexpected, and you have to live in the property. 

If you would like to have a face to face before our next meeting just to chat and talk shop I would love to meet up.

Ask these questions from people you meet face to face.

One suggestion on health insurance is raise your deductible to the highest possible, bare minimum for major medical events, add on a HSA and self insure for everything else. 

Faced with the decision to buy a bunch of less than $100,000 properties in Ohio (for example) that may cash flow $300-800 per month versus a $300,000 property in an appreciating market like Portland, that only cash flows $100-200 per month, I chase the Portland property because in 30 years the value will likely exceed the cumulative cash flow over the year .

So the basement is bare and open.

Worst case scenario we will have the whole street from the hwy to the bay and can build spec houses on it or sell it outright as bare land.