If the current rents are below market, maybe it’s time for some modest increases, from what I’ve heard many landlords do this gradually.

If renting how much will it increase the rent and how long would it take you to make the investment back via the increased rent. 

@Ashish Acharya A big part of my post is highlighting how specific details in local regulations can make it increasingly challenging to operate short-term rentals, even in towns where they’re technically permitted.

Did we see interest rates increase at a rate we've never seen in the last 40+ years?

https://www.har.com/content/department/mlsHouston Real Estate Highlights in November, 2024:-Single-family home sales increased 6.0 percent year-over-year;-Days on Market (DOM) for single-family homes went from 48 to 52 days;-Total property sales were up 3.3 percent with 7,750 units sold;-Total dollar volume rose 11.1 percent to $3.1 billion;-The single-family median price was up 1.5 percent to $329,900;-The single-family average price climbed 4.1 percent to $418,903; -Single-family home months of inventory registered a 4.4-months supply, up from 3.5 months last November.

And they just increased their rental limits to try and keep pace with cash tenants, so if Section 8 is part of your strategy, now is a great time.

My basic assumption is I would be trading a certain level of cash flow for increased appreciation over a period of 10 years.

Doing something faster doesn't mean increasing SPEED!

You're close to the bus stop so you'll attract NYC goers & they move a lot around here.

If you can find properties where you can add value (adding units, increasing rents) then you can increase the value of the property, refi and get your money out.