Sorry, he just ticks me off. 

This burnout led to me selling off my rentals, dissolving my business with family, and having my mother take over managing her own units.

I would greatly appreciate any guidance or advice starting off with this business model.

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.  

I also kept my first home and it is paid off now and worth approximately $150k, with current renters. 

Start off by completing your profile.

In the city or more urban neighborhoods though it's definitely more commonplace.I've added off street parking behind a property off an alley like you said at least a handful of times.

We paid off our primary home last year and have been slowly getting the courage to jump into the investing market where we live in the Pacific Northwest.

Like mentioned it's also beneficial to keep up to date with what's happening in the area your STR is located, and make sure the decision makers are aware of hosts and what they bring to the community.

We took off the carpet and found plywood underneath.