The city’s macro picture is improving with steady population pockets, job growth, and revitalization projects, and even small, well-managed rentals can generate positive cash flow while giving long-term appreciation potential.

I bought my first duplex and fixed up a few basic QoL items and after I moved out I created an LLC and S Corp then hired a part time handyman to be my property manager since I was busy at work and not very handy. 

You are right in that a 1st position cash out is like basically hitting the reset button again.

Once you get it permit-ready, you can get a construction loan, but construction loan lenders want to make sure you are qualified and can execute the project competently since construction has things go wrong a lot.  

Use this period to build “investor muscle”:Network locally: Northern NJ & Northeast PA have active REIA and Mastermind groups where you can learn creative strategies (seller finance, JV, partnerships, DSCR lending, etc.).Educate tactically: Move from general podcasts to deal-focused learning — cash flow calculators, DSCR loan basics, and rent comps.Understand investor financing: Once you’re ready, your pension-backed W2 and equity could make you an excellent DSCR or bridge loan candidate with the right structure.⚙️ 5.

Go to pre app and OH by the way there are late comers fee's attached to that project to the tune of 10k plus per lot. 

Welcome @Liam Davis, Before locking in a location, just focus on understanding the basics of the numbers.

Also, we will be doing many projects before putting the property on str platforms so does the date it is placed in service effect what is deductible in any way or does it not matter?

@Michael KassPlease see below, this is a simple CapEx estimator our team developed to help owners and investors quickly frame project costs and make informed decisions. https://docs.google.com/spreadsheets/d/1ZV7lF9dFJUrtLcrrbkj7DT6oiECnn80W7pub_tZuSSY/edit?

For those, all I do is delete a "projected" value from a row and maybe update the date if it didn't occur when I expected it.