The building next to yours looks much nicer and has THREE security vehicles parked in front.

.- Unfamiliarity of software with my Bookkeeping and Accounting team.Altough not ideal, you may want to pay and do bookkeeping on both platforms for 3 months to see if you 100% want to make the switch.I still use Quickbooks, but the desktop version, it runs perfectly for all my bookkeeping needs.

I'm curious, have you run into any insurance issues? 

App=Spart...If you need a tool to run your deal I have created this free tool that you can use btwhttps://real-estate-tools.com/real-estate-deal-calculator/?

In the long run, I want to have properties that are producing strong cash flow (eventually would love to own small apartment buildings and syndicate larger deals), but it seems that focusing on cash flow and reinvesting those cash flows will be a slower process than focusing on properties prime for appreciation or with opportunities for forced appreciation.

They have a good set of advertisements that focus on their whole house strategy which is good IMHO.We are running about 50/50 on bookings for 2025 right now.

Here is a video that runs down the basics - https://s-media.nyc.gov/agencies/specialenforcement/01-Legal...There is also a prohibited building list - https://www.nyc.gov/site/specialenforcement/registration-law...Here are some more info overall - https://www.nyc.gov/site/specialenforcement/registration-law..All of this makes STRs in the city pretty tough but it certainly not impossible.

Next, run the potential income against construction costs for adding up to four more stories to the building.

We have always said we will run our business, as much as possible, as if it's 10x the size it currently is.

The main issues a lot of investors/PM's run into is the inspection period since Section 8 inspections are no walk in the park.