The increasing barrier to entry results in fewer new STR's coming available for sale, but also fewer options for guests to rent. 

(This option would would not carry any debt, all debt would be paid in cash)Or keep our current house, rent it out, and cash flow NET monthly about $1,500?

In that case, you’d typically need to file a legal challenge, which could involve going to court and showing that the restriction is unnecessary or unreasonable.The best advice I can give would be to consult a real estate attorney to understand your specific situation and options.

As first-time landlords, we considered self-management, but as new parents who work full-time, we decided that hiring a property manager would be the best option for long-term rentals.3.

Much like by the end of this decade, I will take those same steps to become even less involved with work and have more times with my kids who will be really developing and that will be my focus.The difference once I made money, and was able to make it make money for me I de-risked by eliminating leverage.

Two flats are essentially just houses.... they trade like houses and there is a lot of emotion involved.

If you won't be occupying a unit and at least one of the units is occupied by a tenant, you will want to purchase a landlord dwelling policy (there are other options besides a landlord policy but I won't get into that here). 

Are there going to be banks involved, creative seller financing or all cash? 

And this does not even involve business or real estate!

Like Jay said, there can be more flexibility in repayment options.