looking to start real estate development   buying fixing and renting .

. $500k won't buy you much in San Fran but is a pretty healthy budget in Jax.One smaller factor is that Duval county doesn't charge impact fees on new construction (and is the only county in Florida that does not) which is great for developers but not so great when there's no money for maintaining our schools.https://www.jacksonville.com/news/20190423/duval-voters-to-decide-on-proposed-sales-tax-referendum-to-pay-for-replacing-repairing-renovating-schoolsAlso this isn't Florida or Jacksonville specific, but in times when the stock market is particularly volatile real estate investing becomes more appealing even with lower returns.Personally as an investor I find all this out-of-town investing a bit annoying (increased competition and increased prices) and am concerned that these properties potentially aren't well maintained.

I think it would help if you sat down and took the time to identify what YOUR investor profile is.

You should be able to identify the 'leakage'. 

I work for a large development firm here in Milwaukee but am doing my first outside deal.

Nope):1 - Learn how to analyze with real numbers2 - Learn what a plan is, and how to develop one for REI3 - Learn what is important to a REI...and then start thinking like one, instead of a homeowner.4 - Learn how Money Works5 - Learn how to analyze Markets (not economic...geographic) in order to find where the properties whose profiles match the criteria you need to execute the plan you developed.6 - Learn how to eliminate any emotions, both yours and the ones you think are driving forces for the buyers/renters that will be your clients7 - Learn how to eliminate any for of "rationalization" (most expensive word a REI can use) from your thoughts.8...and last, for now, learn how to describe yourself (when asked what you do for a living) as a "Successful Real Estate Investor". 

As has been said already identifying your investment class and investment tolerance, A neighborhoods vs D neighborhoods.

What most syndicators do is market and brand to raise awareness, build credibility and develop relationships.

I use non-traditional national lenders (private equity, Wall St money, insurance companies etc) that I've developed relationships with.  

The west side of town looks more recently developed.