We don't have chimney-specific contractors in Florida and all the roofing contractors don't want to touch it.

When I bought it in 2005 I put on a new roof, int/ext paint, new flooring, new kitchen & bath, new apliances, plumbing, electrical, central heat/air, garage opener, water heater, fence...basically everything! 

For some perspective, that seems like enough money to buy appliances and a hot water heater every year, or replace the roof every 4 years...again, I think.It just doesn't sound right to me.

If we discount future rents using discounted cash flow (DCF), shouldn't we also discount a deferred expense like roof replacement?

A bad roof $5000 discountCarpet &interior paint $2500A stigma from “an unfortunate incident” in a small town?

If a roofer falls off the roof you do not what him/her coming after your home or even visitation rights to your sea snail.I would also recommend writing a solid business plan as one poor decision in the beginning can really mess things up.I look forward to meeting you both at the inevitable PNW Meet-up.

It will need new roof & siding within 3-5yrs.

They may have a bad or nor furnace, leaky roof etc.

As a result, I know there is unmet need especially since my 700 square foot loft which will sleep 4 comfortably and is decked out to the 9's with a roof deck will be AT LEAST $50 to $75 less per night than a Hotel w/ no Kitchen, etc.

New roof?