A one-size-fits-all approach to defining the rules is extraordinarily difficult in the same way that writing down all of the laws in Napoleonic fashion is virtually impossible.

Questions I have as I approach a lease ending in Mid November, 2 months away…-How much notice do I need to give before I ask if they are staying or leaving?

Great approach to notification.

We are open to learn new markets, new type of properties, or even change our approach on things when required. 

This is all me pontificating on my approach, but its basically all up to the strategy you would like to pursue.Either way I would still recommend a 30 year, but here is the logic behind that decision. 30 year loans offer lower payments.

@Dan Guenther or house hack out rooms....tailor the approach to the market..

@Allie Foland I’d owned a bed and breakfast for 24 years but had started working a W-2 job too knowing that the day to sell the B&B was fast approaching.

As for STR's, while I have yet to establish a clear plan for my goals (single vs multi family, etc) I think I am looking for a more hands-off approach than STR's.

If the utility is in the landlords name because of multi unit split there are approaches to dividing those costs and putting it back on the tenant.

I would invite you to rethink HELOCs and slightly tweak your approach.