I’m curious to hear from others with larger portfolios and how they are structured. 

If they refuse, then you have two choices:1.

Whether you plan to rent your current home or buy a new property, the choice depends on your risk tolerance, cash flow goals, and lifestyle preferences.

If you’re nervous, ask for a larger hold back.  

Both are terrible choices NYC, super expensive and high taxes, and TERRIBLE landlord laws.

Feel free to inquire about their staff qualifications if it's a larger organization.2.

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. 

YES, I say LET THEM GO HOMELESS, too damn bad, YOURE CHOICE, I really don't care if you have to live in a tent that you bought by selling your blood, YOU CHOOSE THAT PATH. 

Of larger buildings in DC, there is only 1 single building in DC that allows mid term rentals.

I know I wouldn't have bought it if it was my choice, but it's been passed on to my parents and so I'm just going with the flow here and looking to help them defray the annual costs as much as possible.