Hard lessons to learn in the beginning but the sooner you get there the better.

I'd do it sooner than later.

Outside of real estate, I enjoy the gym, traveling, and cooking. 

I have a nice hi-rise condo unit and I get tons of companies asking if I do MTRs for Visiting Nurses, Tech Professionals, etc.My place is positioned near a number of large DC Metro Hospitals, but since covid work-from-home and recent lift of Eviction Moritorium, I have had few people with jobs, but a ton of people recently evicted looking to rent my place.The one viable group - visiting nurses has been excluded because my HOA will not allow short or mid-term rentals (anything less than one year is a No-No).They claim too many transient tenants cause excessive wear and tear on the property and too many people using resources like the gym, or pool or common areas.I think that's a lot of horse waste!

If I had just called a couple different handymen for quotes, the issue would have been fixed sooner and more professionally.In conclusion, if you want to spend a nontrivial sum each month to make your life more difficult and your work more annoying, Latchel is one way of doing that.

Additionally, consider negotiating the ability to delay or cancel some bookings to complete the necessary work sooner, avoiding further damage.

Something tells me the terms of the funding, if it is real at all, are so onerous that it ultimately comes down to you paying for the opportunity to find them deals.  

If they want to leave, give them 60 - 90 days to find something affordable, but offer to let them leave faster if they find something sooner.

.- I will be able to find tenants sooner in NYC compared to Jacksonville. 

The reality is you're going to use it sooner than if you spread everything out over 27.5 years.