Most owners are local and therefore “hot” money or out of area players are not yet chasing Pittsburgh assets, keeping prices favorable.References United States Census Bureauhttp://www.cmu.edu/news/stories/archives/2017/august/economic-impact-report.htmlMarcus & Millichap 2017 Multifamily Investment Forecast2017 Commercial Real Estate Trends Report by Integra Realty Resourceshttp://www.pittsburghmagazine.com/Pittsburgh-Magazine/September-2017/Staying-CMU-All-Eyes-on-Carnegie-Mellons-Future/http://www.nextpittsburgh.com/features/pittsburgh-developments-watch-2017/

Keep them under my existing Superhost personal account, or set up a new branded account that could stay with the complex forever. 

Staying local and house hacking—especially now, before kids—gives you so much flexibility to set yourselves up for long-term success.Your financial foundation is super strong, and house hacking a quad sounds like an amazing first step for you two.

We have numerous who have their payments set up to auto-pay.

The lessons you learned the hard way in 2008 will be invaluable now, and it’s great that you’re aiming to stay small-scale and within your comfort zone of Sacramento, which gives you an advantage of knowledge in that market.Given your experience, I'd say start by focusing on three key areas to build confidence and minimize risks:Budget Control: Over-renovating was one of the big mistakes you mentioned.

If I own a property with a 1k mortgage per month and it stays empty (or I'm trying to evict) for a couple of months then I'll be ok.

Personally I would stay away from this.  

Hey man I'm staying near Cal state LA not to far from Long beach.

@Nick WimmelYou can get decent cash flow and demand for rentals is likely to stay strong in the area given the proximity to major job centers in Cincinnati and Dayton

Search the BP for ADU appraisals to encounter numerous examples.