Does it improve the roof itself, or does it bring increased maintenance.

2) Is the extra LTV on cash-out worth the increase in interest rate and if not, how much LTV would I need to go get the next property?

It was put in place because the feds have increased immigration for the last ~10 years (over 5M people or 8% of our population) to the point that we now have a housing shortage. 

Market AnalysisDemand: Red River Gorge has seen a significant increase in vacation rental demand. 

Your insurance is going to be highly variable and I wouldn't use what an agent or the seller tells you as the cost of dwelling policies have increased substantially over the past few years due to rising new construction costs. 

The instructor gave a case study where we needed to team up as groups of fours and figure out a way to buy an REO property with no money of our own and increase the equity by 30K.

The shorter the prepayment term has an impact on increasing the rate.4.

Not only would the rent cover your heloc costs (eventually) your property value increases giving you the equity you options for additional real estate investments down the road. 

I believe CA market in general is expected to increase by 4-5% but SF is unique. 

With owner financing, depending on terms offered, we can increase that number by 10 - 20%.