Thank you, Easter BunnyI would make it longer, what you really want to do is sympathize with your target audience so deeply that you are in their shoes.

If I were in your shoes I would put together the strongest argument possible for why the home is worth $275K.

In fact after awhile it will be like breathing or tying your shoes every day. 

You want a house that has a view, that you can showcase on your website. 2. 

I would ask a real estate agent to send me all the listings of properties I could qualify for and I would get the agent to take me out to see 3-5 at a time until I found the one.If I were in your shoes, I would either buy a 'too big house' with conventional or FHA financing and rent spare bedrooms to professionals for $500-900/bedroom (as I've done in the past with my 5 BR 3BA) or I would buy a 2-4 unit multi-unit house and live in one and rent out the others.

It's your decision, but I would cash-in if I were in your shoes.  

You will need a competent on the ground team to watch over your investments, and I would want to meet that team in person if I were in your shoes.

If I were in your shoes would I be mad?...

A good portion of these people will get burned by scenarios like you mention, which is real-life in the shoes of a landlord with multiple units.Somehow these things always seem to come in waves for me too.

Perhaps, more than anything, I'm looking for books and resources chronicling the history of Craftsman homes or showcasing modern restorations.