In a state with no income tax, I'm getting killed by property taxes of 7K a year for each property.

I have a healthy income and have built a solid financial base for my age.

I was able to scale to 4 properties on an entry level income because i was purchasing properties in Sudbury which provided me a high rent relative to the purchase price & mortgage amount.

My accountants won't even touch them because its not economical for them (even if billing by the hour) nor their clients.If you want the kid's Roth to grow, consider how to generate earned income for them. 

For a triplex built in the early 1900's (I'm assuming if it's in the city) in a lower income neighborhood, you should likely be at least $250 for both maintenance and capex per month.

I had just received a 30k down payment from another owner financed deal and I wanted to get a “second home” and get some additional rental income.

I just want the extra monthly income and in 20 years be able to see how much equity I acquired and continue to invest as time goes.

Furthermore, you need at least 14 days of rental income in each of those two tax reporting years. 

I set up my entities mid 2023 -a holding company in WY and an operating LLC in NJ and have only had start up expenses so far and no income.

I lived in the attic instead of using the “livable” space so I could use rental income to pay for the mortgage.