@Rob Elder Wildwood, thanks for the help.

The second house will be a long term rental for my elderly mom. 

Mostly elderly people live in the areas and must travel outside of the areas to do shopping and see doctors. 

Carryout service is provided at no additional charge to individuals living alone who are elderly, ill or disabled and are incapable of conveying their solid waste or recycling container to the designated collection location.

The owner was a very nice elderly man and did not want them to get kicked out right away with the under-market rents so he let them all sign a 1 year lease ending 5/1/2020.

The back story:An elderly member of my fiancé's family has a nice piece of property here in Anchorage that she is going to be selling.

sounds much like a escrow officer out west here when you have a closing with an elderly person they have to meet them in person  or have their personal attorney involved..

I believe this is because the current owner is an elderly lady who lives several hundred miles away, and she is happy to keep the current tenants at below market rates.

(elderly owners limited viewings)  From speaking with the listing agent, the only 'known' issue is 'bow' in the living room where a grand piano has been sitting for many years and the home is dirty.AC unit replaced 2000, unknown age of roof.Finally to my question, I've read J Scotts book, but I'm not 100% comfortable with the estimating part.  

I’m very interested in renting to assisted living companies for elderly as well as handicapped and maybe even oWning an ALF in the future.Any and all information on how to get started, break into that world or advice, tips, hints, gripes, complaints are appreciated!