Section 8 does have challanges but the oppertunity to make multiple income streams and even expand your real estate investmets can become much greater. 

The barrier is the additional complexity - now you are operating two sets of books, and filing two tax returns, and have more operating agreements, more state registrations, etc, need to manage cash better, need to keep in constant mind that your rents need to be a supportable FMV, which may require getting third party certification on your rents so that in the event of an IRS audit, what you have done is supported.In short...the size of the project, and the taxable income, need to be of enough scope to make all the additional costs and annoyances worth it. 

The assets are old, need work constantly, the cost of living is high, and there is no job growth.I wouldn't solely focus on cash flow.

I anticipated constant settle of the fill so the building is on pin piles of course. 

Typically the leaks have been toilets which will constantly run and use water slowly.

I guess the play in this scenario would be the cash from the cash-out refi and the equity growth on the rental property, but nothing in terms of a monthly income stream.

I've also explored manually blocking off the calendar, but this requires constant attention and work. 

After 4 years we have made ZERO percent ROI, this has been a half-time extremely stressful job for us, even with a property manager, with constant repairs and bad tenants.

If you are starting out, I think it makes more sense to chase cash flow to build a solid foundation; then, you can start to add appreciation plays to your portfolio as long as you have a reliable stream of cash flow already coming in. 

My job can be flexible as I run an Airbnb am constantly interacting with guests throughout the day to help with there needs.