If he doesn't want to apply or can't pass your screening due to the lack of SSN, then tell him he can't apply.

The complete lack of understanding is going to do some folks in.The world has a way of working; you reach, it'll teach.

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

Hostaway's lack of transparency in their pricing makes them pretty hard to recommend to anyone since these types of "custom" pricing schemes are often used as a means of upcharging new customers. 

I believe shared housing is going to become more popular, due to the lack of available housing throughout the country; and lenders, insurance, etc. will need to find ways to accommodate their use. 

Either a lack of communication from the tenant's side or a miscommunication from the tenant to their parents.

Lack of gutters on the home and insufficient foundation support led to a new support beam needed underneath the house which will cost $15,000.

I think you're right, the lack of control is probably going to be your biggest emotional hurdle.There may be some middle ground that softens that blow up. 

And do your best not to let the lack of resources dictate your focus or goals.

It goes deeper than that.NYC Liberal policies, including strong tenant protections, increases the risk of failure so much that the risk far outweighs the rewards.Financial ruin is just around the corner for the small Mom and Pop Property Investor that it doesn't make sense for them.The Tenants will have free Attorneys that are bent on delaying eviction cases so long that it stretches into years while Mom and Pop suffer from lack of rental income and still have to pay all the bills and do the management.Additionally, the increase in homeless living rough in the streets due to Sanctuary laws causing a lack of shelter beds, then evicting shelter residents after 30 days creating more homelessness, policies that tie up the Police's ability to arrest perpetrators, etc. only causes Mom and Pop to sell out at large discounts to larger Landlords who are capable to use Economies of Scale to eek out a profit.These larger Landlords will eventually turn a much higher profit as the pendulum will eventually swing towards the middle when the NYC Voting population eventually realizes that it's not a conspiracy of the Rich that's causing the Wealth Gap to increase.It's the same liberal laws that encourage people to become lifelong tenants, small Entrepreneurs (including Property Owners and small Mom and Pop Businesses) to be destroyed, and Rents to rise astronomically as housing becomes scarer even when the population declines by as much as 7% in the last several years.