Full transparency, my wife is concerned we're going to be "downgrading" substantially. (2) any thoughts on what are some of the areas outside SF which lend themselves nicely to what we are trying to accomplish?

It is an older building and has a boiler, which has me concerned.

If it is impossible for you to look at the property prior to purchasing, you MUST have trusted partners that can point out repairs/concerns and estimate (in dollar terms) the remediation plan.  

If your concern is staying close to to your grandfather, then stay close to him in your house hack.

I'm not concerned with the current LTV, the proposed CLTV, any market adjustments, the property's current value, etc. 

They have requested that this fine be taken out of their deposit when they move out, so that may be a little concerning.

The mobile home was a huge concern and I knew it needed to be removed in order to get the best price for the land, so it took some work to find someone who wanted it enough to haul it away himself.

My concern is buying a property around the lake communities (IL, WI, MI) and not having it filled during the winter months. 

If you lie and move into the home, the lender will use this as a defense.I’d be more concerned that you are buying a long-term investment property with hard money when it doesn’t appear you have a viable exit strategy.

Some are going from $1, 000 or less in rent to $1,650 which is concerning to me.