Disagree with this, you still have HVAC, turnover and roof repairs in multifamily which could just as easily wipe out your cash flow. 

I am able to cash flow about $1500 a month on this prop at the moment.

Does your current rental property not cash flow positively?

I havent been able to find anything in my area that pencils out as cash flowing in a LONG time.... but places are still selling fast and above ask, so maybe I'm missing something

I’ve invested considerably into the community to make it better.

It will still be cash flow positive as it can rent for 2200-2300.

From my analysis the cash flow is not much, but I also know beggars can't be choosers lol. 

It's worth paying the taxes if you can earn double the cash flow! 

Lucky for your this is a great real estate investment market and you will find cash flow to be good and appreciation does well in select markets as well.

Older properties could allow for a higher quantity of investments and potentially more cash flow, but I lack experience with these and would consider working with investor friendly realtor and property managers.I would greatly appreciate any advice on:New constructions vs. older homes.Self-managing or working with a property manager.Identifying promising locations for long-term rental investments.Thank you in advance for your time and help.