My biggest piece of advice is to get a killer rental agreement/lease for Cook County.

It's ignorant to say it's without possibility that your over leveraging when a financial institution who has ever incentive to sell you $ says your unsafe to lend more $.

The biggest (that people talk about) is 'due on sale'.  

@Unal Baris KancogluTo manage a multi-family property, communicate rent adjustments early, implement gradual increases, set limits, reassess lease terms, highlight improvements, and offer incentives.

What terms or incentives would be appropriate to attract investors for this timeline?

.- my biggest complain to 401k is actually not the employer matching, but lack of diversfication where I can receive high cash flow with low beta structured portfolio.- for example, although SPY lost 28% their value in 202, but as total return, my portfolio is flat because my dividend income is offsetting the market gain losses.- what I am trying to say is that, if you are a "professional fund manager", you could create your set of portfolio that could beat the market , in this situation , the 401k is even less important.

Right then and there he realized all bills paid was not only an economic burden but it did not put the incentive in the right place, w/the user and was not good for the environment.  

I would tell you the biggest thing is finding which market is a good rental/appreciation area.

Naturally my biggest hurdle is the capital to fund the projects.

If you are looking inside Philly, check the specific area thoroughly - Philly currently has a glut of new construction apartment inventory with amenities and free rent incentives you could be in competition with.