@Jay HinrichsHey jay,If you can come back here to coach status, you can now fly Vegas to Hawaii pretty cheaply on allegiant. 25-50% cheaper at least. 

Maybe do a survey and make sure that the houses are on their own property, not encroaching on another lot.Make sure the ground water is not so high that it floods the basement, house.Make sure there are not a bunch of termites in the ground, and eaten up wood in the houses.Make sure the soil is not shifting, depending on where the houses are located, think sink hole.Check water pressure.Sooo, many things it could be physically.Then you have to look at the social things like the houses getting broken into every other day, neighbors from the hood, or even a building inspector going through a divorce:)  Or maybe it is just something simple like the buyer could not get financed since the house is a wreck, only certain financing is available.

Look at topography and geographic constraints (elevation, water, highways, railways, etc.) as well as social consideration.  

I guess now I’m either waiting for appreciation, or really just the time to go remodel it to at least slumlord status to rent.

You can also buy lists from companies like list source and there are some REI software companies that have a cash buyer search feature.Best way to find motivated sellers is to purchase lists and compile lists from city and county for 60-90-120 days late on mortgage, pre-foreclosure, delinquent taxes, water cutoff, code violation, probate, divorce, high equity, etc. and mail or cold call.Other methods are driving for dollars, door knocking, wholesalers, craigslist, Realtors, FSBO sites, expired listings, foreclosure sites, put out bandit signs, billboards, newspapers, other offline publications.If you have the funds you can run TV commercials, do pay per click/adwords, facebook, Linkedin, Youtube, and other forms of online advertising and social media postings.Bottom line is consistency.

You can also buy lists from companies like list source and there are some REI software companies that have a cash buyer search feature.Best way to find motivated sellers is to purchase lists and compile lists from city and county for 60-90-120 days late on mortgage, pre-foreclosure, delinquent taxes, water cutoff, code violation, probate, divorce, high equity, etc. and mail or cold call.Other methods are driving for dollars, door knocking, wholesalers, craigslist, Realtors, FSBO sites, expired listings, foreclosure sites, put out bandit signs, billboards, newspapers, other offline publications.If you have the funds you can run TV commercials, do pay per click/adwords, facebook, Linkedin, Youtube, and other forms of online advertising and social media postings.Bottom line is consistency.

She currently is on social security and takes 1300 per month from her retirement portfolio.

Really  depends on whether the property is entitled, zoned, utility status etc. hml are usually up for them provided there is a solid exit strategy.

2) I'd refrain from advertising on social media (like BP) how much funds I have to invest!

Although you are adding rent/deposit for the adult (as opposed to a child), you are toeing the line of violating Fair Housing Laws that identifies 'familial status' as a protected class.