I'm also not quite sure if the property values in the higher crime areas will rise at the same level as the surrounding towns. 

You are right that not very many banks will lend at that loan level. 

Your tax implications likely won’t be at the LLC level as most states see LLCs as a pass though, any profits are personally reported.

Let me know if you have any specific tax questions.Just so you are awarePA does not follow the federal guidelines for 1031 exchanges(does't apply in your case if you are flipping but i thought i'd let you know if you were thinking of alternative exit opportunities).Also PA does not recognize NOL's at the state level for individuals.

It comes down to your level of liquidity and your comfort level.

I would be using an FHA loan and obviously don't believe Milwaukee will be at the same fenzied level as Boston but would like to gauge the market as I begin to plan.Happy to connect with local resources to discuss options. 

Then focus on the 1-3 strategies that can both accomplish your goals and incorporate your experience level.

I would be using an FHA loan and obviously don't believe Milwaukee will be at the same fenzied level as Boston but would like to gauge the market as I begin to plan.Happy to connect with local resources to discuss options. 

I've started seeing some recommendations around using Land Trusts as a way to acquire your properties and then use no more than 2 LLCs to complete the Asset strategy picture here.

A number of buyers such as REITs, retirees, family trusts, and passive investors who want the tax benefits.