@Chris Seveney, I would first say it depends on your goals, whether you are boots on the ground local or not, and what you're bringing to the deal making table.If you need a flow of deals, you probably need to be on those wholesalers' lists, a good agent, and to do some mailer prospecting.

How to respond depends on whether you want to keep him as a tenant.  

This really depends on your financial situation.

Some insurance agents are still sending me the proof each year...So, i guess it depends on your state and locatlity... 

 There are advantages to both depending on your situation.

It depends what the purpose are you trying to achieve when you're tapping/pulling the funds from your house.

Depending on how close you want to get to $300K will probably depend on the city and what age you are willing to consider. 

As long as you are negative cash flowing less than what you would be paying in rent, it makes sense (this depends on your market; I am in Austin, and nothing here has positive cash flow).

We agree that it absolutely depends on your design intent, including the number of stories and square footage, hillside vs flat and overall level of custom detail desired.

The HELOC has a start rate of Prime 8.5+ 3 ish, depends what your FICO is.