GM and Chrysler Headquarters borders the small town, ect. 

Before making the plunge, I highly advise you to consult with a cross-border tax & legal specialist to determine the best entity structure to use.

Credit is an issue across borders and an income in one country while investing in another country makes lenders nervous.If you are really planning on living in FL, I would at least focus on FL if you buy.

Just inside PA on the DE border.

However, I am not 100 percent sure this would be consistent income so it's kind of a gamble.

When you add in the ocean and southern border, the reality is you've got half the land supply options most other markets have.That's why RE is so expensive here and why it's likely to continue being so. 

Should I wait and gamble that they won’t sell so I can do a conventional loan to buy both? 

@Julio CorderoYou need to get with a CPA and cross border tax consultant as part of your team of advisors.

If I understand you correctly, you are advising a sort of modified brrrr strategy - modified since these houses are owned already but strategically pulling out a conservative amount of debt.The houses are mostly C class but some border on B-.

I see it as more of a gamble than an investment.